List of organic reactions
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Well-known reactions
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s in organic chemistry
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Organic reaction
Organic reactions are chemical reactions involving organic compounds. The basic organic chemistry reaction types are addition reactions, elimination reactions, substitution reactions, pericyclic reactions, rearrangement reactions, photochemical reactions and redox reactions. In organic synthesis,...
and reagent
Reagent
A reagent is a "substance or compound that is added to a system in order to bring about a chemical reaction, or added to see if a reaction occurs." Although the terms reactant and reagent are often used interchangeably, a reactant is less specifically a "substance that is consumed in the course of...
s in organic chemistry
Organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, composition, reactions, and preparation of carbon-based compounds, hydrocarbons, and their derivatives...
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A
- Abramovitch-Shapiro tryptamine synthesis
- AcetalisationAcetalisationAcetalisation is an organic reaction that involves the formation of an acetal or ketal. One way of acetal formation is the nucleophilic addition of an alcohol to a ketone or an aldehyde...
- Acetoacetic ester condensation
- Achmatowicz reactionAchmatowicz reactionThe Achmatowicz Reaction is an organic synthesis in which a furan is converted to a dihydropyran. In the original publication by Osman Achmatowicz Jr. in 1971 furfuryl alcohol is reacted with bromine in methanol to 2,5-dimethoxy-2,5-dihydrofuran which rearranges to the dihydropyran with dilute...
- AcylationAcylationIn chemistry, acylation is the process of adding an acyl group to a compound. The compound providing the acyl group is called the acylating agent....
- Acyloin condensationAcyloin condensationAcyloin condensation is a reductive coupling of two carboxylic esters using metallic sodium to yield an α-hydroxyketone, also known as an acyloin....
- Adams catalyst
- Adkins catalystAdkins catalystCopper chromite is a complex inorganic composition Cu2Cr2O5, but often containing barium oxide that is used to catalyse certain reactions in organic synthesis. It was first described in 1908. A variety of composition are recognized including Cr2CuO4·CuO·BaCrO4 and Cr2Cu2O5...
- Adkins-Peterson reactionAdkins-Peterson reactionThe Adkins-Peterson reaction is the air oxidation of methanol to formaldehyde with metal oxide catalysts such as iron oxide, molybdenum trioxide or combinations thereof.It was developed by Homer Burton Adkins and Wesley R. Peterson.- References :#...
- Akabori amino acid reactionAkabori amino acid reactionThere are several Akabori Amino Acid Reactions1.1. In the first an α-amino acid is oxidised by heating it with an oxidizing sugar.2. In the second an α-amino acids and esters are reduced by sodium amalgam and ethanolic HCl to give α-amino aldehydes....
- Alcohol oxidationAlcohol oxidationAlcohol oxidation is an important organic reaction. Primary alcohols can be oxidized either to aldehydes or to carboxylic acids , while the oxidation of secondary alcohols normally terminates at the ketone stage...
- Alder ene reaction
- Alder-Stein rules
- Aldol addition
- Aldol condensationAldol condensationAn aldol condensation is an organic reaction in which an enol or an enolate ion reacts with a carbonyl compound to form a β-hydroxyaldehyde or β-hydroxyketone, followed by a dehydration to give a conjugated enone....
- Algar-Flynn-Oyamada reactionAlgar-Flynn-Oyamada reactionThe Algar–Flynn–Oyamada reaction is a chemical reaction whereby a chalcone undergoes an oxidative cyclization to form a flavonol.-Reaction mechanism:...
- Alkylimino-de-oxo-bisubstitutionAlkylimino-de-oxo-bisubstitutionAlkylimino-de-oxo-bisubstitution in organic chemistry is the organic reaction of carbonyl compounds with amines to imines . The reaction name is based on the IUPAC Nomenclature for Transformations...
- Alkyne trimerisationAlkyne trimerisationAn alkyne trimerisation reaction is a 2+2+2 cyclization reaction in which three alkyne molecules react to form an aromatic compound. The reaction is 'pseudo' pericyclic since it has not been observed to occur without the assistance of metal catalysis; and the metal catalyst assembles the ring...
- Alkyne zipper reactionAlkyne zipper reactionThe alkyne zipper reaction is an organic reaction which isomerizes an organic compound containing an internal alkyne into a terminal alkyne. This was first reported by Charles Allen Brown and Ayako Yamashita in 1975...
- Allan-Robinson reactionAllan-Robinson reactionThe Allan-Robinson reaction is the chemical reaction of o-hydroxyaryl ketones with aromatic anhydrides to form flavones .Note that if aliphatic anhydrides are used, coumarins can also be formed. -Mechanism:...
- Allylic rearrangementAllylic rearrangementAn allylic rearrangement or allylic shift is an organic reaction in which the double bond in an allyl chemical compound shifts to the next carbon atom. It is encountered in nucleophilic substitution....
- Amadori rearrangementAmadori rearrangementThe amadori rearrangement is an organic reaction describing the acid or base catalyzed isomerization or rearrangement reaction of the N-glycoside of an aldose or the glycosylamine to the corresponding 1-amino-1-deoxy-ketose...
- Amine alkylationAmine alkylationAmine alkylation is a type of organic reaction between an alkyl halide and ammonia or an amine. The reaction is called nucleophilic aliphatic substitution , and the reaction product is a higher substituted amine...
- Angeli-Rimini reactionAngeli-Rimini reactionThe Angeli-Rimini reaction is an organic reaction between an aldehyde and the sulfonamide N-hydroxybenzenesulfonamide in presence of base forming an hydroxamic acid....
- Andrussov oxidation
- Appel reactionAppel reactionThe Appel reaction is an organic reaction that converts an alcohol into an alkyl chloride using triphenylphosphine and carbon tetrachloride. The use of carbon tetrabromide or bromine as a halide source will yield alkyl bromides, whereas using methyl iodide or iodine gives alkyl iodides...
- Arbuzov reaction, Arbusow reaction
- Arens-van Dorp synthesis, Isler modification
- Aromatic nitrationNitrationNitration is a general chemical process for the introduction of a nitro group into a chemical compound. The dominant application of nitration is for the production of nitrobenzene, the precursor to methylene diphenyl diisocyanate...
- Arndt-Eistert synthesisArndt-Eistert synthesisThe Arndt-Eistert synthesis is a series of chemical reactions designed to convert a carboxylic acid to a higher carboxylic acid homologue and is considered a homologation process...
- Auwers synthesisAuwers synthesisThe Auwers synthesis is a series of organic reactions forming a flavonol from a coumarone. This reaction was first reported by Karl von Auwers in 1908....
- Azo couplingAzo couplingAn azo coupling is an organic reaction between a diazonium compound and a dialkylaniline , phenol or other aromatic compound which produces an azo compound. In this reaction the diazonium salt is an electrophile and the activated arene is a nucleophile in an electrophilic aromatic substitution...
B
- Baeyer-Drewson indigo synthesisBaeyer-Drewson indigo synthesisThe Baeyer–Drewson indigo synthesis is an organic reaction in which indigo is prepared from 2-nitrobenzaldehyde and acetone The reaction is classified as a Aldol condensation...
- Baeyer-Villiger oxidationBaeyer-Villiger oxidationThe Baeyer–Villiger oxidation is an organic reaction in which a ketone is oxidized to an ester by treatment with peroxy acids or hydrogen peroxide. Key features of the Baeyer–Villiger oxidation are its stereospecificity and predictable regiochemistry...
- Baeyer-Villiger rearrangement
- Bakeland process (Bakelite)
- Baker-Venkataraman rearrangementBaker-Venkataraman rearrangementThe Baker–Venkataraman rearrangement is the chemical reaction of 2-acetoxyacetophenones with base to form 1,3-diketones.This rearrangement reaction proceeds via enolate formation followed by acyl transfer...
, Baker-Venkataraman transformation - Bally-Scholl synthesis
- Balz-Schiemann reaction
- Bamberger rearrangementBamberger rearrangementThe Bamberger rearrangement is the chemical reaction of N-phenylhydroxylamines with strong aqueous acid, which will rearrange to give 4-aminophenols...
- Bamberger triazine synthesisBamberger triazine synthesisThe Bamberger triazine synthesis in organic chemistry is a classic organic synthesis of a triazine first reported by Eugen Bamberger in 1892 ....
- Bamford-Stevens reactionBamford-Stevens reactionThe Bamford–Stevens reaction is a chemical reaction whereby treatment of tosylhydrazones with strong base gives alkenes. It is named for the British chemist William Randall Bamford and the Scottish chemist Thomas Stevens Stevens...
- Barbier-Wieland degradation
- Bardhan-Senguph phenanthrene synthesis
- Barfoed's testBarfoed's testBarfoed's Test is a chemical test used for detecting the presence of monosaccharides. It is based on the reduction of copper acetate to copper oxide , which forms a brick-red precipitate....
- Bartoli indole synthesisBartoli indole synthesisThe Bartoli indole synthesis is the chemical reaction of ortho-substituted nitroarenes with vinyl grignard reagents to form substituted indoles....
, Bartoli reaction - Barton reactionBarton reactionThe Barton Reaction involves the photolysis of a nitrite to form a δ-nitroso alcohol. It is named for the British chemist Sir Derek Harold Richard Barton...
- Barton-Kellogg reactionBarton-Kellogg reactionThe Barton-Kellogg reaction is a coupling reaction between a ketone and a thioketone through a diazo intermediate forming an alkene.This reaction has been pioneered by Hermann Staudinger and therefore the reaction also goes by the name Staudinger type diazo-thioketone coupling.- Reaction mechanism...
- Barton-McCombie reaction, Barton deoxygenation
- Barton Zard SynthesisBarton Zard SynthesisThe Barton-Zard Synthesis method of pyrrole synthesis is a cyclisation reaction between a nitroalkene and α-isocyanoacetate under base conditions.-Mechanism:It consists in three main steps:...
- Barton vinyl iodine procedureHydrazone iodinationHydrazone iodination is an organic reaction in which a hydrazone is converted into a vinyl iodide by reaction of iodine and a non-nucleophilic base such as DBU. First published by D. H. R...
- Baudisch reactionBaudisch reactionThe Baudisch Reaction was discovered by Oskar Baudisch in 1939 and further developed by his colleague Cronheim. In the reaction a solution containing aqueous hydroxylamine hydrochloride and hydrogen peroxide reacts with benzene or phenol, with the assistance of copper to give o-nitrosophenols...
- Bayer test
- Baylis-Hillman reaction
- Bechamp reactionBechamp reactionIn organic synthesis, the Bechamp reaction is used for producing arsonic acids from activated aromatic rings such as aniline. It was first described by A. J. Bechamp in 1863. The reaction is an electrophilic aromatic substitution, using arsenic acid as a reactant.One example of an important arsonic...
- Bechamp reductionBechamp ReductionThe Bechamp reduction is used to reduce aromatic nitro compounds to their corresponding anilines, using iron and hydrochloric acid.This reaction was originally used to produce large amounts of aniline for industry, but catalytic hydrogenation is the preferred method...
- Beckmann fragmentation
- Beckmann rearrangementBeckmann rearrangementThe Beckmann rearrangement, named after the German chemist Ernst Otto Beckmann , is an acid-catalyzed rearrangement of an oxime to an amide...
- Bellus-Claisen rearrangement
- Belousov-Zhabotinsky reactionBelousov-Zhabotinsky reactionA Belousov–Zhabotinsky reaction, or BZ reaction, is one of a class of reactions that serve as a classical example of non-equilibrium thermodynamics, resulting in the establishment of a nonlinear chemical oscillator. The only common element in these oscillating systems is the inclusion of bromine...
- Benary reactionBenary reactionThe Benary reaction is an organic reaction. In 1931 Erich Bénary discovered that β--vinyl ketones reacted with Grignard reagents in a 1,4-addition to give α,β-unsaturated ketones, α,β-unsaturated aldehydes and α,β-unsaturated esters as well as poly-unsaturated ketones and aldehydes after hydrolysis...
- Benedict's reagentBenedict's reagentBenedict's reagent is a chemical reagent named after an American chemist, Stanley Rossiter Benedict....
- Benkeser reactionBenkeser ReactionThe Benkeser reduction reaction is the catalytic hydrogenation of polycyclic aromatic hydrocarbons, especially naphthalene using lithium or calcium metal and any of the following primary amines or low molecular weight alkyl groups as reductants: -CH3, -CH2CH3, -CH2CH2CH3, -CH2CH2NH2.This reaction...
- Benzidine rearrangement
- Benzilic acid rearrangementBenzilic acid rearrangementThe benzilic acid rearrangement is the rearrangement reaction of benzil with potassium hydroxide to benzilic acid. First performed by Justus Liebig in 1838 this reaction type is displayed by 1,2-diketones in general...
- Benzoin condensationBenzoin condensationThe benzoin condensation is a reaction between two aromatic aldehydes, particularly benzaldehyde. The reaction is catalyzed by a nucleophile such as the cyanide anion or an N-heterocyclic carbene. The reaction product is an aromatic acyloin with benzoin as the parent compound...
- Bergman cyclizationBergman cyclizationThe Bergman cyclization or Bergman reaction or Bergman cycloaromatization is an organic reaction and more specifically a rearrangement reaction taking place when an enediyne is heated in presence of a suitable hydrogen donor . It is named for the American chemist Robert George Bergman...
- Bergmann azlactone peptide synthesis
- Bergmann degradationBergmann degradationThe Bergmann degradation is a series of chemical reactions designed to remove a single amino acid from the carboxylic acid end of a peptide.The acyl azide of a peptide undergoes a Curtius rearrangement in the presence of benzyl alcohol to give a benzyl carbamate...
- Bergmann-Zervas carbobenzoxy method
- Bernthsen acridine synthesisBernthsen acridine synthesisThe Bernthsen acridine synthesis is the chemical reaction of a diarylamine heated with a carboxylic acid and zinc chloride to form a 9-substituted acridine....
- Bestmann's reagent
- Betti reactionBetti reactionThe Betti reaction is a chemical reaction of aldehydes, primary aromatic amines and phenols producing α-aminobenzylphenols. The Betti reaction is a special case of the Mannich reaction.-References:...
- Biginelli pyrimidine synthesis
- Biginelli reactionBiginelli reactionThe Biginelli reaction is a multiple-component chemical reaction that creates 3,4-dihydropyrimidin-2-ones 4 from ethyl acetoacetate 1, an aryl aldehyde , and urea 3. It is named for the Italian chemist Pietro Biginelli.This reaction was developed by Pietro Biginelli in 1891...
- Birch reductionBirch reductionThe Birch Reduction is an organic reaction which is particularly useful in synthetic organic chemistry. The reaction was reported in 1944 by the Australian chemist Arthur Birch working in the Dyson Perrins Laboratory in the University of Oxford, building on earlier work by Wooster and Godfrey in...
- Bischler-Möhlau indole synthesisBischler-Möhlau indole synthesisThe Bischler-Möhlau indole synthesis is a chemical reaction that forms a 2-aryl-indole from an α-bromo-acetophenone and excess aniline.In spite of its long history, this classical reaction has received relatively little attention in comparison with other methods for indole synthesis, perhaps owing...
- Bischler-Napieralski reactionBischler-Napieralski reactionThe Bischler–Napieralski reaction is an intramolecular electrophilic aromatic substitution reaction that allows for the cyclization of β-arylethylamides or β-arylethylcarbamates. It was first discovered in 1893 by August Bischler and Bernard Napieralski, in affiliation with Basle Chemical Works and...
- Biuret testBiuret testThe biuret test is a chemical test used for detecting the presence of peptide bonds. In the presence of peptides, a copper ion forms a violet-colored complex in an alkaline solution...
- Blaise ketone synthesisBlaise ketone synthesisThe Blaise ketone synthesis is the chemical reaction of acid chlorides with organozinc compounds to give ketones. The reaction also works with organocuprates.Reviews have been written...
- Blaise reactionBlaise reactionThe Blaise reaction is an organic reaction that forms a β-ketoester from the reaction of zinc metal with a α-bromoester and a nitrile. The final intermediate is a metaloimine, which is hydrolyzed to give the desired β-ketoester....
- Blanc reaction
- Blanc chloromethylationBlanc chloromethylationThe Blanc chloromethylation is the chemical reaction of aromatic rings with formaldehyde and hydrogen chloride catalyzed by zinc chloride to form chloromethyl arenes.-References:# Gustave Louis Blanc Bull. Soc. Chim. France 1923, 33, 313....
- Bodroux reaction
- Bodroux-Chichibabin aldehyde synthesisBodroux-Chichibabin aldehyde synthesisThe Bodroux-Chichibabin aldehyde synthesis is a chemical reaction whereby a Grignard reagent is converted to an aldehyde one carbon longer.Reaction of a Grignard reagent with triethyl orthoformate gives an acetal, which can be hydrolyzed to an aldehyde. For example, the synthesis of n-hexanal:...
- Bogert-Cook synthesis
- Bohn-Schmidt reaction
- Boord olefin synthesisBoord olefin synthesisThe Boord olefin synthesis is an organic reaction forming alkenes from ethers carrying a halogen atom 2 carbons removed from the oxygen atom catalyzed by a metal such as magnesium or zinc. The reaction, discovered by Cecil E...
- Borodin reaction
- Borsche-Drechsel cyclization
- Bosch-Meiser urea process
- Bouveault aldehyde synthesisBouveault aldehyde synthesisThe Bouveault aldehyde synthesis is a one-pot chemical reaction that converts a primary alkyl halide to an aldehyde one carbon longer.-Reaction mechanism:The first step of the Bouveault aldehyde synthesis is the formation of the Grignard reagent...
- Bouveault-Blanc reductionBouveault-Blanc reductionThe Bouveault-Blanc reduction is a chemical reaction in which an ester is reduced to primary alcohols using absolute ethanol and sodium metal.This reaction is an inexpensive and large-scale alternative to lithium aluminium hydride reduction of esters....
- Boyland-Sims oxidationBoyland-Sims oxidationThe Boyland-Sims oxidation is the chemical reaction of anilines with alkaline potassium persulfate, which after hydrolysis forms ortho-hydroxyl anilines.The ortho-isomer is formed predominantly...
- Boyer Reaction
- Bredt's ruleBredt's RuleBredt's rule is an empirical observation in organic chemistry that states that a double bond cannot be placed at the bridgehead of a bridged ring system, unless the rings are large enough...
- Brown hydroboration
- Bucherer carbazole synthesisBucherer carbazole synthesisThe Bucherer carbazole synthesis is a chemical reaction used to synthesize carbazoles from naphthols and aryl hydrazines using sodium bisulfite. The reaction is named after Hans Theodor Bucherer.-References:...
- Bucherer reactionBucherer reactionThe Bucherer reaction in organic chemistry is the reversible conversion of naphthol to naphthylamine in presence of ammonia and sodium bisulfite ....
- Bucherer–Bergs reaction
- Buchner ring enlargement
- Buchner-Curtius-Schlotterbeck reaction
- Buchwald-Hartwig amination
- Bunnett reaction
C
- Cadiot-Chodkiewicz couplingCadiot-Chodkiewicz couplingThe Cadiot-Chodkiewicz coupling in organic chemistry is a coupling reaction between a terminal alkyne and a haloalkyne catalyzed by a copper salt such as copper bromide and an amine base. The reaction product is a di-acetylene or di-alkyne....
- Camps quinoline synthesisCamps quinoline synthesisThe Camps quinoline synthesis is a chemical reaction whereby an o-acylaminoacetophenone is transformed into two different hydroxyquinolines using hydroxide ion....
- Cannizzaro reactionCannizzaro reactionThe Cannizzaro reaction, named after its discoverer Stanislao Cannizzaro, is a chemical reaction that involves the base-induced disproportionation of an aldehyde lacking a hydrogen atom in the alpha position...
- Carbohydrate acetalisationCarbohydrate acetalisationIn carbohydrate chemistry carbohydrate acetalisation is an organic reaction and a very effective means of providing a protecting group. The example below depicts the acetalisation reaction of D-ribose 1. With acetone or 2,2-dimethoxypropane as the acetalisation reagent the reaction is under...
- Carbonyl reductionCarbonyl reductionCarbonyl reduction in organic chemistry is the organic reduction of any carbonyl group containing compound by a reducing agent. Typical carbonyl compounds are ketones , aldehydes, carboxylic acids and esters. A carbonyl group can be reduced to the alcohol or the oxygen atom can be removed...
- CarbonylationCarbonylationCarbonylation refers to reactions that introduce carbon monoxide into organic and inorganic substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemistry.-Organic chemistry:...
- Carbylamine reactionCarbylamine reactionThe Carbylamine reaction is a chemical test for detection of primary amines. In this reaction, the analyte is heated with alcoholic potassium hydroxide and chloroform...
- Carroll reaction
- Castro-Stephens couplingCastro-Stephens couplingThe Castro-Stephens Coupling is a cross coupling reaction between a copper acetylide and an aryl halide forming a disubstituted alkyne and a copper halide....
- Catalytic reformingCatalytic reformingCatalytic reforming is a chemical process used to convert petroleum refinery naphthas, typically having low octane ratings, into high-octane liquid products called reformates which are components of high-octane gasoline...
- CBS reductionCBS reductionThe Corey-Itsuno Reduction, also known as the Corey-Bakshi-Shibata reduction, is a chemical reaction in which an achiral ketone is enantioselectively reduced to produce the corresponding chiral, non-racemic alcohol...
- Chan-Lam coupling
- Chapman rearrangement
- Cheletropic reactionCheletropic reactionthumb|300px|right|Pericyclic ReactionsCheletropic reactions are a type of pericyclic reaction. A pericyclic reaction is one that involves a transition state with a cyclic array of atoms and an associated cyclic array of interacting orbitals. A reorganization of σ and π bonds occurs in this cyclic...
- Chichibabin pyridine synthesisChichibabin pyridine synthesisThe Chichibabin pyridine synthesis -chē-bā-bēn) is a method for synthesizing pyridine rings. In its general form, the reaction can can be described as a condensation reaction of aldehydes, ketones, α,β-Unsaturated carbonyl compounds, or any combination of the above, in ammonia or ammonia...
- Chichibabin reactionChichibabin reactionThe Chichibabin reaction -chē-bā-bēn) is a method for producing 2-aminopyridine derivatives by the reaction of pyridine with sodium amide. It was reported by Aleksei Chichibabin in 1914. The following is the overall form of the general reaction:...
- Chiral pool synthesisChiral pool synthesisChiral pool synthesis is a strategy that aims to improve the efficiency of chiral synthesis. It starts the organic synthesis of a complex enantiopure chemical compound from a stock of readily available enantiopure substances. Common chiral starting materials include monosaccharides and amino acids...
- Chugaev eliminationChugaev eliminationThe Chugaev elimination is a chemical reaction that involves the elimination of water from alcohols to produce alkenes. The intermediate is a xanthate. It is named for its discoverer, the Russian chemist Lev Aleksandrovich Chugaev....
- Ciamician-Dennstedt rearrangement
- Claisen condensationClaisen condensationThe Claisen condensation is a carbon–carbon bond forming reaction that occurs between two esters or one ester and another carbonyl compound in the presence of a strong base, resulting in a β-keto ester or a β-diketone...
- Claisen rearrangementClaisen rearrangementThe Claisen rearrangement is a powerful carbon-carbon bond-forming chemical reaction discovered by Rainer Ludwig Claisen...
- Claisen-Schmidt condensation
- Clemmensen reductionClemmensen reductionClemmensen reduction is a chemical reaction described as a reduction of ketones to alkanes using zinc amalgam and hydrochloric acid. This reaction is named after Erik Christian Clemmensen, a Danish chemist....
- Collins-Reagent
- Combes quinoline synthesisCombes quinoline synthesisThe Combes quinoline synthesis is a chemical reaction involving the condensation of unsubstituted anilines with β-diketones to form substituted quinolines after an acid-catalyzed ring closure of an intermediate Schiff base .-See also:*Conrad-Limpach reaction*Doebner reaction*Doebner-Miller...
- Conia reaction
- Conrad-Limpach synthesisConrad-Limpach synthesisThe Conrad-Limpach synthesis is the chemical reaction of anilines with β-ketoesters to form 4-hydroxyquinolines via a Schiff base .Several reviews have been published.-References:...
- Corey-Gilman-Ganem oxidation
- Cook-Heilbron thiazole synthesisCook-Heilbron thiazole synthesisThe Cook-Heilbron thiazole synthesis is the chemical reaction of α-aminonitriles with carbon disulfide to form 5-amino-2-mercapto-thiazoles....
- Cope elimination
- Cope rearrangementCope rearrangementThe Cope rearrangement is an extensively studied organic reaction involving the [3,3]-sigmatropic rearrangement of 1,5-dienes. It was developed by Arthur C. Cope...
- Corey reagent
- Corey-Bakshi-Shibata reduction
- Corey-Fuchs reactionCorey-Fuchs reactionThe Corey–Fuchs reaction, also known as the Ramirez–Corey–Fuchs reaction, is a series of chemical reactions designed to transform an aldehyde into an alkyne. The formation of the 1,1-dibromoolefins via phosphine-dibromomethylenes was originally discovered by Desai, McKelvie and Ramirez...
- Corey-Kim oxidationCorey-Kim oxidationThe Corey–Kim oxidation is an oxidation reaction used to synthesise aldehydes and ketones from primary and secondary alcohols. It is named for American chemist and Nobelist Elias James Corey and Korean-American chemist Choung Un Kim....
- Corey-Posner, Whitesides-House reaction
- Corey-Winter olefin synthesisCorey-Winter olefin synthesisThe Corey-Winter olefin synthesis is a series of chemical reactions for converting 1,2-diols into olefins. It is named for the American chemist and Nobelist Elias James Corey and the American-Estonian chemist Roland Arthur Edwin Winter....
- Corey-Winter reaction
- Coupling reactionCoupling reactionA coupling reaction in organic chemistry is a catch-all term for a variety of reactions where two hydrocarbon fragments are coupled with the aid of a metal catalyst...
- Craig method
- Cram's rule of asymmetric induction
- Creighton processCreighton processThe Creighton process involves the hydrogenation of a 6 carbon chain alcohol. The reactant is 2,3,4,5,6-pentahydroxyhexanal The Creighton process involves the hydrogenation of a 6 carbon chain alcohol. The reactant is 2,3,4,5,6-pentahydroxyhexanal The Creighton process involves the hydrogenation...
- Criegee reaction
- Criegee rearrangementCriegee rearrangementThe Criegee rearrangement is a rearrangement reaction named after Rudolf Criegee. In this organic reaction a tertiary alcohol is cleaved in an organic oxidation by a peroxyacid to a ketone...
- Cross metathesis
- Crum Brown-Gibson rule
- Curtius degradation
- Curtius rearrangementCurtius rearrangementThe Curtius rearrangement , as first defined by Theodor Curtius, is a chemical reaction that involves the rearrangement of an acyl azide to an isocyanate. Several reviews have been published....
, Curtius reaction - Cyanohydrin reactionCyanohydrin reactionA Cyanohydrin reaction is an organic chemical reaction by an aldehyde or ketone with a cyanide anion or a nitrile to form a cyanohydrin. This nucleophilic addition is a reversible reaction but with aliphatic carbonyl compounds equilibrium is in favor of the reaction products. The cyanide source...
D
- Dakin reactionDakin reactionThe Dakin oxidation is an organic redox reaction in which an ortho- or para-hydroxylated phenyl aldehyde or ketone reacts with hydrogen peroxide in base to form a benzenediol and a carboxylate[3]...
- Dakin-West reactionDakin-West reactionThe Dakin–West reaction is a chemical reaction that transforms an amino-acid into a keto-amide using an acid anhydride and a base, typically pyridine. It is named for Henry Drysdale Dakin and Randolph West . Of special note, the keto-amide product is always racemic.With pyridine as a base and...
- Danheiser AnnulationDanheiser AnnulationThe Danheiser annulation or Danheiser TMS-cyclopentene annulation is an organic reaction of an α,β-unsaturated ketone and a trialkylsilylallene in the presence of a Lewis Acid to give a trialkylsilylcyclopentene in a regiocontrolled annulation....
- Darapsky degradation
- Darzens condensation, Darzens-Claisen reaction, Glycidic ester condensation
- Darzens synthesis of unsaturated ketones
- Darzens tetralin synthesis
- Dehydration reactionDehydration reactionIn chemistry and the biological sciences, a dehydration reaction is usually defined as a chemical reaction that involves the loss of water from the reacting molecule. Dehydration reactions are a subset of elimination reactions...
- DehydrogenationDehydrogenationDehydrogenation is a chemical reaction that involves the elimination of hydrogen . It is the reverse process of hydrogenation. Dehydrogenation reactions may be either large scale industrial processes or smaller scale laboratory procedures....
- Delepine reactionDelepine reactionThe Delépine reaction is the organic synthesis of primary amines by reaction of a benzyl or alkyl halides with hexamethylenetetramine followed by acid hydrolysis of the quaternary ammonium salt...
- Demjanov rearrangementDemjanov rearrangementThe Demjanov rearrangement is the chemical reaction of primary amines with nitrous acid to give rearranged alcohols. It involves substitution by a hydroxyl group with a possible ring expansion. It is named after the Russian chemist Nikolai Jakovlevich Demjanov...
- Demjanow desamination
- Dess-Martin oxidation
- Diazoalkane 1,3-dipolar cycloadditionDiazoalkane 1,3-dipolar cycloadditionThe Diazoalkane 1,3-dipolar cycloaddition is a 1,3-dipolar cycloaddition between a 1,3-dipole diazo compound and a dipolarophile. When the dipolarphile is an alkene, the reaction product is a pyrazoline....
- Diazotisation
- DIBAL-H selective reduction
- Dieckmann condensationDieckmann condensationThe Dieckmann condensation is the intramolecular chemical reaction of diesters with base to give β-ketoesters. It is named after the German chemist Walter Dieckmann . The equivalent intermolecular reaction is the Claisen condensation....
- Dieckmann reaction
- Diels-Alder reactionDiels-Alder reactionThe Diels–Alder reaction is an organic chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene system. The reaction can proceed even if some of the atoms in the newly formed ring are not carbon...
- Diels Reese reactionDiels Reese reactionThe Diels Reese Reaction was first reported in 1934 by O. Diels and J. Reese. An extension to the reaction was made by William Hearon. The reaction is believe to proceed through an unknown intermediate or adduct as proposed by Hearon. By changing the solvent the resulting product will change. ...
- Dienol benzene rearrangement
- Dienone phenol rearrangement
- Dimroth rearrangementDimroth rearrangementThe Dimroth rearrangement is a rearrangement reaction taking place with certain 1,2,3-triazoles where endocyclic and exocyclic nitrogen atoms switch place . This organic reaction was discovered in 1909 by Otto Dimroth ....
- Di-pi-methane rearrangementDi-pi-methane rearrangementThe di-pi-methane rearrangement is a photochemical reaction of a molecular entity comprising two π-systems, separated by a saturated carbon atom , to form an ene- substituted cyclopropane...
- Directed ortho metalationDirected ortho metalationDirected ortho metalation is an adaptation of electrophilic aromatic substitution in which electrophiles attach themselves exclusively to the ortho- position of a direct metalation group or DMG through the intermediary of an aryllithium compound . The DMG interacts with lithium through a hetero atom...
- Doebner modification
- Doebner reactionDoebner reactionThe Doebner reaction is the chemical reaction of an aniline with an aldehyde and pyruvic acid to form quinoline-4-carboxylic acids....
- Doebner-Miller reactionDoebner-Miller reactionThe Doebner-Miller reaction is the organic reaction of an aniline with α,β-unsaturated carbonyl compounds to form quinolines.This reaction is also known as the Skraup-Doebner-Von Miller quinoline synthesis, and is named after the Czech chemist Zdenko Hans Skraup , and the Germans Oscar Döbner and...
, Beyer method for quinolines - Doering-LaFlamme carbon chain extension
- Dötz reactionDötz reactionThe Wulff-Dötz reaction is the chemical reaction of an aromatic or vinylic alkoxy pentacarbonyl chromium carbene complex with an alkyne and carbon monoxide to give a Cr3-coordinated substituted phenol. Several reviews have been published...
- Dowd-Beckwith ring expansion reactionDowd-Beckwith ring expansion reactionThe Dowd–Beckwith ring expansion reaction is an organic reaction in which a cyclic β-keto ester is expanded by up to 4 carbons in a free radical ring expansion reaction through an α-alkylhalo substituent . The radical initiator system is based on AIBN and tributyltin hydride. The cyclic β-keto...
- Duff reactionDuff reactionThe Duff reaction or hexamine aromatic formylation is a formylation reaction used in organic chemistry for the synthesis of benzaldehydes with hexamine as the formyl carbon source...
- Dutt-Wormall reaction
- Dyotropic reactionDyotropic reactionA dyotropic Reaction in organic chemistry is a type of organic reaction and more specifically a pericyclic valence isomerization in which two sigma bonds simultaneously migrate intramolecularly...
E
- E1cB elimination reactionE1cB elimination reactionThe E1cB elimination reaction is a special type of elimination reaction in organic chemistry. This reaction mechanism explains the formation of alkenes from alkyl halides through a carbanion intermediate given specified reaction conditions and specified substrates. The abbreviation stands for ...
- Eder reaction
- Edman degradationEdman degradationEdman degradation, developed by Pehr Edman, is a method of sequencing amino acids in a peptide. In this method, the amino-terminal residue is labeled and cleaved from the peptide without disrupting the peptide bonds between other amino acid residues....
- Eglinton reaction
- Ehrlich-Sachs reaction
- Einhorn variant
- Einhorn-Brunner reactionEinhorn-Brunner reactionThe Einhorn-Brunner reaction is the chemical reaction of imides with alkyl hydrazines to form a mixture of isomeric 1,2,4-triazoles.-References:...
- Elbs persulfate oxidationElbs persulfate oxidationThe Elbs persulfate oxidation is the organic reaction of phenols with alkaline potassium persulfate to form para-diphenols.Several reviews have been published.-Reaction mechanism:...
- Elbs reactionElbs reactionThe Elbs reaction is an organic reaction describing the pyrolysis of an ortho methyl substituted benzophenone to condensed polyaromatic. The reaction is named after its inventor, the German chemist Karl Elbs also responsible for the Elbs oxidation...
- Electrochemical fluorinationElectrochemical fluorinationElectrochemical fluorination , or electrofluorination, is a foundational organofluorine chemistry method for the preparation of fluorocarbon-based organofluorine compounds. The general approach represents an application of electrosynthesis...
- Electrocyclic reactionElectrocyclic reactionIn organic chemistry, an electrocyclic reaction is a type of pericyclic rearrangement reaction where the net result is one pi bond being converted into one sigma bond or vice-versa...
- Electrophilic halogenationElectrophilic halogenationIn organic chemistry, an electrophilic aromatic halogenation is a type of electrophilic aromatic substitution. This organic reaction is typical of aromatic compounds and a very useful method for adding substituents to an aromatic system....
- Electrophilic aminationElectrophilic aminationElectrophilic amination is a chemical process involving the formation of a carbon–nitrogen bond through the reaction of a nucleophilic carbanion with an electrophilic source of nitrogen.-Introduction:...
- Elimination reactionElimination reactionAn elimination reaction is a type of organic reaction in which two substituents are removed from a molecule in either a one or two-step mechanism...
- Emde degradationEmde degradationThe Emde degradation is a method for the reduction of a quaternary ammonium cation to a tertiary amine with sodium amalgam...
- Emmert reaction
- Ene reactionEne reactionThe Ene reaction is a chemical reaction between an alkene with an allylic hydrogen and a compound containing a multiple bond , in order to form a new σ-bond with migration of the ene double bond and 1,5 hydrogen shift. The product is a substituted alkene with the double bond shifted to the...
- Enyne metathesisEnyne metathesisAn Enyne metathesis is an organic reaction taking place between an alkyne and an alkene with a metal carbene catalyst forming a butadiene. This reaction is a variation of olefin metathesis.The general scheme is given by scheme 1:...
- Epoxidation
- Erlenmeyer synthesis, Azlactone synthesis
- Erlenmeyer-Plöchl azlactone and amino acid synthesisErlenmeyer-Plöchl azlactone and amino acid synthesisThe Erlenmeyer-Plochl azlactone and amino acid synthesis, named after Friedrich Gustav Carl Emil Erlenmeyer who partly discovered the reaction, is a series of chemical reactions which transform glycine to various other amino acids via an oxazolone and an azlactone.Hippuric acid self-condenses in...
- Eschenmoser fragmentationEschenmoser fragmentationThe Eschenmoser fragmentation, first published in 1967, is the chemical reaction of α,β-epoxyketones with aryl sulfonylhydrazines to give alkynes and carbonyl compounds...
- Eschweiler-Clarke reactionEschweiler-Clarke reactionThe Eschweiler–Clarke reaction is a chemical reaction whereby a primary amine is methylated using excess formic acid and formaldehyde. Reductive amination reactions such as this one will not produce quaternary ammonium salts, but instead will stop at the tertiary amine stage...
- Ester pyrolysisEster pyrolysisEster pyrolysis in organic chemistry is a vacuum pyrolysis reaction converting esters containing a β-hydrogen atom into the corresponding carboxylic acid and the alkene...
- Ether cleavageEtherEthers are a class of organic compounds that contain an ether group — an oxygen atom connected to two alkyl or aryl groups — of general formula R–O–R'. A typical example is the solvent and anesthetic diethyl ether, commonly referred to simply as "ether"...
- Étard reactionEtard ReactionThe Étard reaction is a chemical reaction that involves the direct oxidation of an aromatic or heterocyclic bound methyl group to an aldehyde using chromyl chloride. It is named for the French chemist Alexandre Léon Étard...
- Evans aldol
F
- Favorskii reactionFavorskii reactionThe Favorskii reaction , named for the Russian chemist Alexei Yevgrafovich Favorskii, is a special case of nucleophilic attack on a carbonyl group involving a terminal alkyne with acidic protons....
- Favorskii rearrangementFavorskii rearrangementThe Favorskii rearrangement , named for the Russian chemist Alexei Yevgrafovich Favorskii, is most principally a rearrangement of cyclopropanones and α-halo ketones which leads to carboxylic acid derivatives. In the case of cyclic α-halo ketones, the Favorski rearrangement constitutes a ring...
- Favorskii-Babayan synthesis
- Fehling testFehling's solutionFehling's solution is a chemical test used to differentiate between water-soluble aldehyde and ketone functional groups, and as a test for monosaccharides. The test was developed by German chemist Hermann von Fehling in 1849.-Laboratory preparation:...
- Feist-Benary synthesisFeist-Benary synthesisThe Feist-Benary synthesis is an organic reaction between α-halogen ketones and β-dicarbonyl compounds to substituted furan compounds. This condensation reaction is catalyzed by amines such as ammonia and pyridine. The first step in the ring synthesis is related to the Knoevenagel condensation...
- Fenton reaction
- Ferrario reaction
- Ferrier carbocyclizationFerrier carbocyclizationThe Ferrier carbocyclization is an organic reaction that was first reported by the carbohydrate chemist Robert J. Ferrier in 1979. It is a metal-mediated rearrangement of enol ether pyrans to cyclohexanones...
- Ferrier rearrangementFerrier rearrangementThe Ferrier rearrangement is an organic reaction that involves a nucleophilic substitution reaction combined with an allylic shift in a glycal . It was discovered by the carbohydrate chemist Robert J...
- Finkelstein reactionFinkelstein reactionThe Finkelstein reaction, named for the German chemist Hans Finkelstein , is an SN2 reaction that involves the exchange of one halogen atom for another...
- Fischer indole synthesisFischer indole synthesisThe Fischer indole synthesis isa chemical reaction that produces the aromatic heterocycle indole from a phenylhydrazine and an aldehyde or ketone under acidic conditions. The reaction was discovered in 1883 by Hermann Emil Fischer. Today antimigraine drugs of the triptan class are often...
- Fischer oxazole synthesisFischer oxazole synthesisThe Fischer oxazole synthesis is a chemical synthesis of the aromatic heterocycle oxazole from cyanohydrins and aldehydes in the presence of anhydrous hydrochloric acid. This method was discovered by Hermann Emil Fischer in 1896.-References:...
- Fischer peptide synthesis
- Fischer phenylhydrazine and oxazone reaction
- Fischer glycosidationFischer glycosidationFischer glycosidation refers to the formation of a glycoside by the reaction of an aldose or ketose with an alcohol in the presence of an acid catalyst...
- Fischer-Hepp rearrangementFischer-Hepp rearrangementThe Fischer-Hepp rearrangement is a rearrangement reaction in which an aromatic N-nitroso or nitrosamine converts to a carbon nitroso compound:This organic reaction was first described by the German chemist Otto Philipp Fischer and...
- Fischer-Speier esterification
- Fischer Tropsch synthesis
- Fleming-Tamao oxidationFleming-Tamao oxidationThe Fleming–Tamao oxidation is the organic oxidation of alkyl silanes into alcohols with peroxides. The research groups of Fleming and Tamao developed procedures for this reaction in parallel to one another. It is especially useful since it allows alcohols to be masked as much more resilient...
- Flood reaction
- Folin-Ciocalteu reagentFolin-Ciocalteu reagentThe Folin–Ciocalteu reagent or Folin's phenol reagent or Folin–Denis reagent, also called the Gallic Acid Equivalence method , is a mixture of phosphomolybdate and phosphotungstate used for the colorimetric assay of phenolic and polyphenolic antioxidants...
- Formox processFormox processThe Formox process produces formaldehyde. Formox is a worldwide registered trademark owned by Perstorp Specialty Chemicals AB, Sweden.Industrially, formaldehyde is produced by catalytic oxidation of methanol. The most commonly used catalysts are silver metal or a mixture of an iron oxide with...
- Forster reaction
- Forster-Decker methodForster-Decker methodThe Forster-Decker method is a series of chemical reactions that transform a primary amine ultimately to a secondary amine . The first step is the formation of a Schiff base , followed by alkylation, and hydrolysis.-References:...
- Fowler Process
- Franchimont reaction
- Frankland synthesis
- Frankland-Duppa reaction
- Free radical halogenationFree radical halogenationIn organic chemistry, free-radical halogenation is a type of halogenation. This chemical reaction is typical of alkanes and alkyl-substituted aromatics under application of heat or UV light. The reaction is used for the industrial synthesis of chloroform , dichloromethane , and hexachlorobutadiene...
- Freund reaction
- Friedel-Crafts AcylationFriedel-Crafts reactionThe Friedel–Crafts reactions are a set of reactions developed by Charles Friedel and James Crafts in 1877. There are two main types of Friedel–Crafts reactions: alkylation reactions and acylation reactions. This reaction type is a form of electrophilic aromatic substitution...
- Friedel-Crafts AlkylationFriedel-Crafts reactionThe Friedel–Crafts reactions are a set of reactions developed by Charles Friedel and James Crafts in 1877. There are two main types of Friedel–Crafts reactions: alkylation reactions and acylation reactions. This reaction type is a form of electrophilic aromatic substitution...
- Friedländer synthesisFriedländer synthesisThe Friedländer synthesis is the chemical reaction of 2-aminobenzaldehydes with ketones to form quinoline derivatives. It is named after German chemist Paul Friedländer ....
- Fries rearrangementFries rearrangementThe Fries rearrangement, named for the German chemist Karl Theophil Fries, is a rearrangement reaction of a phenyl ester to a hydroxy aryl ketone by catalysis of Lewis acids.It involves migration of an acyl group of phenyl ester to benzene ring.- Mechanism:...
- Fritsch-Buttenberg-Wiechell rearrangementFritsch-Buttenberg-Wiechell rearrangementThe Fritsch–Buttenberg–Wiechell rearrangement, named for Paul Ernst Moritz Fritsch, Wilhelm Paul Buttenberg, and Heinrich G. Wiechell, is a chemical reaction whereby a 1,1-diaryl-2-bromo-alkene rearranges to a 1,2-diaryl-alkyne by reaction with a strong base such as an alkoxide.This rearrangement...
- Fujimoto-Belleau reactionFujimoto-Belleau reactionThe Fujimoto-Belleau reaction is a chemical reaction that forms cyclic α-substituted α,β-unsaturated ketones from enol lactones. The reaction is named after the two chemists George I. Fujimoto and Bernard Belleau....
- Fukuyama couplingFukuyama couplingThe Fukuyama coupling is a coupling reaction taking place between a thioester and an organozinc halide in the presence of a palladium catalyst. The reaction product is a ketone. This reaction was discovered by Tohru Fukuyama et al. in 1998...
- Fukuyama indole synthesisFukuyama indole synthesisThe Fukuyama indole synthesis is the chemical reaction of alkenylthioanilides to give 2,3-disubstituted indoles. Most commonly tributyltin hydride is utilized as the reducing agent, with azobisisobutyronitrile as a radical initiator....
- Fukuyama reductionFukuyama reductionThe Fukuyama reduction is an organic reaction and an organic reduction in which a thioester is reduced to an aldehyde by a silyl hydride in presence of a catalytic amount of palladium. This reaction was invented in 1990 by Tohru Fukuyama...
G
- Gabriel ethylenimine method
- Gabriel synthesisGabriel synthesisThe Gabriel synthesis is named for the German chemist Siegmund Gabriel. Traditionally, it is a chemical reaction that transforms primary alkyl halides into primary amines using potassium phthalimide....
- Gabriel-Colman rearrangementGabriel-Colman rearrangementThe Gabriel-Colman rearrangement is the chemical reaction of phthalimidoacetic esters with strong base to form substituted isoquinolines ....
, Gabriel isoquinoline synthesis - Gallagher-Hollander degradationGallagher-Hollander degradationIn the Gallagher-Hollander Degradation pyruvic acid is removed from a linear aliphatic carboxylic acid yielding a new acid with 2 carbon atoms less...
- Gassman indole synthesisGassman indole synthesisThe Gassman indole synthesis is a series of chemical reactions used to synthesize substituted indoles from aniline.This is a one-pot chemical reaction, and none of the intermediates are isolated. R1 can be hydrogen or alkyl, while R2 works best with aryl, but can also be alkyl...
- Gastaldi synthesis
- Gattermann aldehyde synthesis
- Gattermann Koch reaction
- Gattermann reactionGattermann reactionThe Gattermann rection, named for the German chemist Ludwig Gattermann, in organic chemistry refers to a reaction of hydrocyanic acid with an aromatic compound, in this case benzene, under catalysis with Friedel-Crafts catalyst .Catalyst used is Copper Powder in HX in the case of reaction of...
- Geminal halide hydrolysisGeminal halide hydrolysisGeminal halide hydrolysis is an organic reaction. The reactants are a geminal dihalide and water or a hydroxide. The reaction product is a ketone or an aldehyde. The first part of the reaction mechanism consists of an ordinary nucleophilic aliphatic substitution to produce a gem-halohydrin...
- Gewald reactionGewald reactionThe Gewald reaction is an organic reaction involving the condensation of a ketone with a α-cyanoester in the presence of elemental sulfur and base to give a poly-substituted 2-amino-thiophene. -Reaction mechanism:...
- Gibbs phthalic anhydride process
- Gilman reagentGilman reagentA Gilman reagent is a lithium and copper reagent compound, R2CuLi, where R is an organic radical. These are useful because they react with organic chlorides, bromides, and iodides to replace the halide group with an R group. This is extremely useful in creating larger molecules from smaller...
- Glaser coupling
- Glycol cleavageGlycol cleavageGlycol cleavage is a specific type of organic chemistry oxidation. The carbon–carbon bond in a Glycol cleavage is a specific type of organic chemistry oxidation. The carbon–carbon bond in a Glycol cleavage is a specific type of organic chemistry oxidation. The carbon–carbon bond in a (vicinal diol...
- Gomberg-Bachmann reactionGomberg-Bachmann reactionThe Gomberg–Bachmann reaction, named for the Ukrainian-American chemist Moses Gomberg and the American chemist Werner Emmanuel Bachmann, is an aryl-aryl coupling reaction via a diazonium salt....
- Gomberg-Bachmann-Hey reaction
- Gomberg-Free radical reaction
- Gould-Jacobs reactionGould-Jacobs reactionThe Gould-Jacobs reaction is an organic synthesis for the preparation of quinolines. In this reaction aniline or an aniline derivative first reacts with malonic acid derivative ethyl ethoxymethylenemalonate with substitution of the ethoxy group by nitrogen. A benzannulation takes place by...
- Graebe-Ullmann synthesis
- Grignard degradation
- Grignard reactionGrignard reactionThe Grignard reaction is an organometallic chemical reaction in which alkyl- or aryl-magnesium halides add to a carbonyl group in an aldehyde or ketone. This reaction is an important tool for the formation of carbon–carbon bonds...
- Grob fragmentationGrob fragmentationA Grob fragmentation, named for the British chemist Cyril A. Grob, is an elimination reaction taking place when an electrofuge and nucleofuge are situated in positions 1 and 3 on an aliphatic chain...
- Groove synthesis
- Grubbs' catalystGrubbs' catalystGrubbs' Catalyst is a transition metal carbene complex named after Robert H. Grubbs, the chemist who first synthesized it. There are two generations of the catalyst, as shown on the right. In contrast to other olefin metathesis catalysts, Grubbs' Catalysts tolerate other functional groups in the...
in Olefin metathesisOlefin metathesisOlefin metathesis or transalkylidenation is an organic reaction that entails redistribution of alkylene fragments by the scission of carbon - carbon double bonds in olefins . Its advantages include the creation of fewer sideproducts and hazardous wastes. Yves Chauvin, Robert H. Grubbs, and Richard R... - Grundmann aldehyde synthesisGrundmann aldehyde synthesisThe Grundmann aldehyde synthesis is a chemical reaction that produces an aldehyde from an acyl halide.Because of the Rosenmund reduction and DIBAL-H accomplish similar transformations, this reaction sequence is not practiced much currently....
- Gryszkiewicz-Trochimowski and McCombie method
- Guareschi-Thorpe condensation
- Guerbet reactionGuerbet reactionThe Guerbet reaction, named after Marcel Guerbet , is an organic reaction converting a primary aliphatic alcohol into its β-alkylated dimer alcohol with loss of one equivalent of water. This reaction requires a catalyst and elevated temperatures....
- Gutknecht pyrazine synthesis
H
- Haller-Bauer reaction
- Haloform reactionHaloform reactionThe haloform reaction is a chemical reaction where a haloform is produced by the exhaustive halogenation of a methyl ketone in the presence of a base. R may be , alkyl or aryl...
- Halogen addition reactionHalogen addition reactionA halogen addition reaction is a simple organic reaction where a halogen molecule is added to the carbon–carbon double bond of an alkene functional group.The general chemical formula of the halogen addition reaction is:...
- Halohydrin formation reactionHalohydrin formation reactionThe halohydrin formation reaction is a chemical reaction in which a halogen is added to an alkene in aqueous solution to form a halohydrin. The reaction is a form of electrophilic addition; it is similar to the halogen addition reaction....
- Hammett equationHammett equationThe Hammett equation in organic chemistry describes a linear free-energy relationship relating reaction rates and equilibrium constants for many reactions involving benzoic acid derivatives with meta- and para-substituents to each other with just two parameters: a substituent constant and a...
- Hammick reactionHammick reactionThe Hammick reaction, named after Dalziel Hammick, is a chemical reaction described as a thermal decarboxylation of α-picolinic acids in the presence of carbonyl compounds to form 2-pyridyl-carbinols....
- Hammond-Principle or Hammond postulate
- Hantzsch pyrrole synthesisHantzsch pyrrole synthesisThe Hantzsch pyrrole synthesis, named for Arthur Rudolf Hantzsch, is the chemical reaction of β-ketoesters with ammonia and α-haloketones to give substituted pyrroles ....
- Hantzsch dihydropyridine synthesis, Hantzsch pyridine synthesisHantzsch pyridine synthesisThe Hantzsch pyridine synthesis or Hantzsch dihydropyridine synthesis is a multi-component organic reaction between an aldehyde such as formaldehyde, 2 equivalents of a β-keto ester such as ethyl acetoacetate and a nitrogen donor such as ammonium acetate or ammonia. The initial reaction product is...
- Hantzsch Pyridine synthesisHantzsch pyridine synthesisThe Hantzsch pyridine synthesis or Hantzsch dihydropyridine synthesis is a multi-component organic reaction between an aldehyde such as formaldehyde, 2 equivalents of a β-keto ester such as ethyl acetoacetate and a nitrogen donor such as ammonium acetate or ammonia. The initial reaction product is...
, Gattermann-Skita synthesis, Guareschi-Thorpe condensation, Knoevenagel-Fries modification - Hantzsch-Collidin-synthesis
- Harber-Weiss reactionHarber-Weiss reactionThe Haber-Weiss reaction generates •OH from H2O2 and superoxide . This reaction can occur in cells and is therefore a possible source for oxidative stress. The reaction is very slow, but is catalyzed by iron...
- Harries ozonide reaction
- Haworth methylation
- Haworth Phenanthrene synthesis
- Haworth-reaction
- Hay coupling
- Hayashi rearrangementHayashi rearrangementThe Hayashi rearrangement is the chemical reaction of ortho-benzoylbenzoic acids catalyzed by sulfuric acid or phosphorus pentoxide.This reaction proceeds through electrophilic acylium ion attack with a spiro intermediate....
- Heck reactionHeck reactionThe Heck reaction is the chemical reaction of an unsaturated halide with an alkene and a base and palladium catalyst to form a substituted alkene. Together with the other palladium-catalyzed cross-coupling reactions, this reaction is of great importance, as it allows one to do substitution...
- Helferich method
- Hell-Volhard-Zelinsky halogenationHell-Volhard-Zelinsky halogenationThe Hell-Volhard-Zelinsky halogenation reaction halogenates carboxylic acids at the α carbon. The reaction is named after three chemists, the German chemists Carl Magnus von Hell and Jacob Volhard and the Russian chemist Nikolay Zelinsky .- Scheme :Unlike other halogenation reactions, this...
- Hemetsberger indole synthesisHemetsberger indole synthesisThe Hemetsberger indole synthesis is a chemical reaction that thermally decomposes a 3-aryl-2-azido-propenoic ester into an indole-2-carboxylic ester.Yields are typically above 70%...
- Hemetsberger-Knittel synthesis
- Henkel reaction, Raecke process, Henkel process
- Henry reaction, Kamlet reaction
- Herz reactionHerz reactionThe Herz-reaction, named after the chemist Richard Herz, is the chemical conversion of an aniline-derivative to a so-called Herz-salt with disulfur dichloride, followed by hydrolysis of this Herz-salt to the corresponding sodium thiolate :-Benzothiazoles:The sodium thiolate 3 can be converted to...
, Herz compounds - Herzig-Meyer alkimide group determination
- Heumann indigo synthesis
- Hydration reactionHydration reactionIn organic chemistry, a hydration reaction is a chemical reaction in which a hydroxyl group and a hydrogen cation are added to the two carbon atoms bonded together in the carbon-carbon double bond which makes up an alkene functional group. The reaction usually runs in a strong acidic, aqueous...
- HydroaminationHydroaminationThe hydroamination reaction is the addition of an N-H bond across the C=C or C≡C bonds of an alkene or alkyne. This is a highly atom economical method of preparing substituted amines that are attractive targets for organic synthesis and the pharmaceutical industry.The hydroamination reaction is...
- HydrodesulfurizationHydrodesulfurizationHydrodesulfurization is a catalytic chemical process widely used to remove sulfur from natural gas and from refined petroleum products such as gasoline or petrol, jet fuel, kerosene, diesel fuel, and fuel oils...
- HydrogenolysisHydrogenolysisHydrogenolysis is a chemical reaction whereby a carbon–carbon or carbon–heteroatom single bond is cleaved or undergoes "lysis" by hydrogen. The heteroatom may vary, but it usually is oxygen, nitrogen, or sulfur. A related reaction is hydrogenation, where hydrogen is added to the molecule, without...
- HydrosilylationHydrosilylationHydrosilylation, also called catalytic hydrosilation, describes the addition of Si-H bonds across unsaturated bonds. Ordinarily the reaction is conducted catalytically and usually the substrates are unsaturated organic compounds. Alkenes and alkynes give alkyl and vinyl silanes; aldehydes and...
- Hinsberg indole synthesis
- Hinsberg oxindole synthesisHinsberg oxindole synthesisThe Hinsberg oxindole synthesis is a method of preparing oxindoles from the bisulfite adducts of glyoxal....
- Hinsberg reactionHinsberg reactionThe Hinsberg reaction is a chemical test for the detection of amines.It is an excellent test for distinguishing primary,secondary and tertiary amines.In this test, the amine is shaken well with Hinsberg reagent in the presence of aqueous alkali . A reagent containing an aqueous sodium hydroxide...
- Hinsberg separation
- Hinsberg sulfone synthesis
- Hoch-Campbell ethylenimine synthesis
- Hock rearrangement
- Hofmann degradation, Exhaustive methylation
- Hofmann eliminationHofmann eliminationHofmann elimination is a process where an amine is reacted to create a tertiary amine and an alkene by treatment with excess methyl iodide followed by treatment with silver oxide, water, and heat.After the first step, a quaternary ammonium iodide salt is created...
- Hofmann Isonitrile synthesis, Carbylamine reactionCarbylamine reactionThe Carbylamine reaction is a chemical test for detection of primary amines. In this reaction, the analyte is heated with alcoholic potassium hydroxide and chloroform...
- Hofmann produkt
- Hofmann rearrangementHofmann rearrangementThe Hofmann rearrangement is the organic reaction of a primary amide to a primary amine with one fewer carbon atom.The reaction is named after its discoverer: August Wilhelm von Hofmann...
- Hofmann-Löffler reactionHofmann-Löffler reactionThe Hofmann-Löffler reaction is an organic reaction in which a cyclic amine 2 is generated by thermal or photochemical decomposition of N-halogenated amine 1 in the presence of a strong acid...
, Löffler-Freytag reaction, Hofmann-Löffler-Freytag reaction - Hofmann-Martius rearrangementHofmann-Martius rearrangementThe Hofmann–Martius rearrangement in organic chemistry is a rearrangement reaction converting an N-alkylated aniline to the corresponding ortho and / or para aryl-alkylated aniline...
- Hofmann's Rule
- Hofmann-Sand reaction
- Homo rearrangement of steroids
- Hooker reactionHooker reactionIn the Hooker reaction an alkyl chain in a certain naphthoquinone is reduced by one methylene unit as carbon dioxide in each potassium permanganate oxidation....
- Horner-Wadsworth-Emmons reactionHorner-Wadsworth-Emmons reactionThe Horner-Wadsworth-Emmons reaction is the chemical reaction of stabilized phosphonate carbanions with aldehydes to produce predominantly E-alkenes....
- Hoesch reaction
- Hosomi-Sakurai reaction
- Houben-Fischer synthesis
- Hudlicky fluorinationFluorination with aminosulfuranesFluorination with aminosulfuranes is a chemical reaction that transforms oxidized organic compounds into organofluorine compounds. Aminosulfuranes selectively exchange hydroxyl groups for fluorine, but are also capable of converting carbonyl groups, halides, silyl ethers, and other functionality...
- Hunsdiecker reactionHunsdiecker reactionThe Hunsdiecker reaction is the organic reaction of silver salts of carboxylic acids with halogens to give organic halides. It is an example of a halogenation reaction...
- Hydroboration
- Hydrocarbon crackingCracking (chemistry)In petroleum geology and chemistry, cracking is the process whereby complex organic molecules such as kerogens or heavy hydrocarbons are broken down into simpler molecules such as light hydrocarbons, by the breaking of carbon-carbon bonds in the precursors. The rate of cracking and the end products...
- HydrohalogenationHydrohalogenationA hydrohalogenation reaction is the electrophilic addition of hydrohalic acids like hydrogen chloride or hydrogen bromide to alkenes to yield the corresponding haloalkanes....
I
- Ing-Manske procedure
- Ipso substitution
- Ishikawa reagentIshikawa reagentIshikawa's reagent is a fluorinating reagent used in organic chemistry. It is used to convert alcohols into alkyl fluorides and carboxylic acids into acyl fluorides. Aldehydes and ketones do not react with it. The reagent consists of a mixture of N,N-diethyl-amine and...
- trans-cis isomerismIsomerIn chemistry, isomers are compounds with the same molecular formula but different structural formulas. Isomers do not necessarily share similar properties, unless they also have the same functional groups. There are many different classes of isomers, like stereoisomers, enantiomers, geometrical...
- Ivanov reagent, Ivanov reactionIvanov reactionThe Ivanov reaction is the chemical reaction of the dianions of aryl acetic acids with electrophiles, primarily carbonyl compounds or isocyanates...
J
- Jacobsen epoxidationJacobsen epoxidationThe Jacobsen Epoxidation, sometimes also referred to as Jacobsen-Katsuki Epoxidation is a chemical reaction which allows enantioselective epoxidation of unfunctionalized alkyl- and aryl- substituted olefins. It is complementary to the Sharpless epoxidation...
- Jacobsen rearrangementJacobsen rearrangementThe Jacobsen rearrangement is a chemical reaction, commonly described as the migration of an alkyl group in a sulfonic acid derived from a polyalkyl- or polyhalobenzene:...
- Janovsky reaction
- Japp-Klingemann reactionJapp-Klingemann reactionThe Japp-Klingemann reaction is a chemical reaction used to synthesize hydrazones from β-keto-acids and aryl diazonium salts. The Reaction is named after the chemists Francis Robert Japp and Felix Klingemann....
- Japp-Maitland condensationJapp-Maitland condensationThe Japp-Maitland condensation is an organic reaction and a type of Aldol reaction and a tandem reaction. In a reaction between the ketone 2-pentanone and the aldehyde benzaldehyde catalyzed by base the bis Aldol adduct is formed first...
- Johnson-Claisen rearrangement
- Jones oxidationJones oxidationThe Jones oxidation, is an organic reaction for the oxidation of primary and secondary alcohols to carboxylic acids and ketones, respectively. It is named after its discoverer, Sir Ewart Jones....
- Jordan-Ullmann-Goldberg synthesis
- Julia olefinationJulia olefinationThe Julia olefination is the chemical reaction of phenyl sulfones with aldehydes to give alkenes after alcohol functionalization and reductive elimination using sodium amalgam or SmI2...
- Julia–Lythgoe olefination
K
- Kabachnik–Fields reaction
- Kharasch–Sosnovsky reaction
- Ketone halogenationKetone halogenationIn organic chemistry ketone halogenation is a special type of halogenation.The position alpha to the carbonyl group in a ketone is easily halogenated, due to the ability to form an enolate in basic solution, or an enol in acidic solution...
- Kiliani–Fischer synthesis
- Kindler reaction
- Kishner cyclopropane synthesis
- Knoevenagel condensationKnoevenagel condensationThe Knoevenagel condensation reaction is an organic reaction named after Emil Knoevenagel. It is a modification of the Aldol condensation.A Knoevenagel condensation is a nucleophilic addition of an active hydrogen compound to a carbonyl group followed by a dehydration reaction in which a molecule...
- Knorr pyrazole synthesis
- Knorr pyrrole synthesisKnorr pyrrole synthesisThe Knorr pyrrole synthesis is a widely used chemical reaction that synthesizes substituted pyrroles '. The method involves the reaction of an α-amino-ketone ' and a compound containing a methylene group α- to a carbonyl group '.-Method:The mechanism requires zinc and acetic acid as catalysts...
- Knorr quinoline synthesisKnorr quinoline synthesisThe Knorr quinoline synthesis is an intramolecular organic reaction converting a β-ketoanilide to a 2-hydroxyquinoline using sulfuric acid. This reaction was first described by Ludwig Knorr in 1886...
- Koch–Haaf reaction
- Kochi reactionKochi reactionThe Kochi reaction is an organic reaction for the decarboxylation of carboxylic acids to alkyl halides with lead tetraacetate and a lithium chloride or other lithium salts .The reaction is a variation of the Hunsdiecker reaction....
- Koenigs–Knorr reaction
- Kolbe electrolysisKolbe electrolysisKolbe electrolysis or Kolbe reaction is an organic reaction named after Adolph Wilhelm Hermann Kolbe. The Kolbe reaction is formally a decarboxylative dimerisation and proceeds by a radical reaction mechanism...
- Kolbe–Schmitt reaction
- König method
- Kornblum oxidationKornblum oxidationThe Kornblum oxidation is a chemical reaction of a primary halide with dimethyl sulfoxide to form an aldehyde.Like all DMSO-based oxidations, the Kornblum oxidation creates an alkoxysulphonium ion, which, in the presence of a base, such as triethylamine , will eliminate to form the desired aldehyde....
- Kornblum–DeLaMare rearrangementKornblum–DeLaMare rearrangementThe Kornblum–DeLaMare rearrangement is a rearrangement reaction in organic chemistry in which a primary or secondary organic peroxide is converted to the corresponding ketone and alcohol under base catalysis...
- Kostanecki acylationKostanecki acylationThe Kostanecki acylation is a method used in organic synthesis to form chromones or coumarins by acylation of o-hydroxyaryl ketones with aliphatic acid anhydrides, followed by cyclization:-Mechanism:...
- Kowalski ester homologationKowalski ester homologationThe Kowalski ester homologation is a chemical reaction for the homologation of esters.This reaction was designed as a safer alternative to the Arndt-Eistert synthesis. The Kowalski reaction is named after its inventor, Conrad J. Kowalski....
- Krapcho decarboxylationKrapcho decarboxylationThe Krapcho decarboxylation is the chemical reaction of esters with halide anions. The ester must contain an electron-withdrawing group in the beta position, such as β-ketoesters, malonic esters, α-cyanoesters, or α-sulfonylesters. It works best with methyl esters, since it is basically a...
- Kröhnke aldehyde synthesis
- Kröhnke oxidation
- Kröhnke pyridine synthesis
- Kucherov reaction
- Kuhn–Winterstein reaction
- Kulinkovich reactionKulinkovich reactionThe Kulinkovich reaction describes the organic synthesis of cyclopropanols via reaction of esters with dialkyldialkoxytitanium reagents, generated in situ from Grignard reagents bearing hydrogen in beta-position and titanium alkoxides such as titanium isopropoxide. This reaction was discovered by...
- Kumada couplingKumada couplingA Kumada coupling or Kumada-Corriu coupling is a cross coupling reaction in organic chemistry between an alkyl or aryl Grignard reagent and an aryl or vinyl halocarbon catalysed by nickel or palladium. This reaction is relevant to organic synthesis because it gives access to styrene derivatives...
L
- Larock indole synthesisLarock indole synthesisThe Larock indole synthesis is a chemical reaction used to synthesize indoles from ortho-iodoanilines and a disubstituted alkyne.An excess of alkyne, using palladium carbonate or palladium acetate and a base, and adding one equivalent of lithium chloride tend to give the best yields...
- Lebedev process
- Lehmstedt-Tanasescu reactionLehmstedt-Tanasescu reactionThe Lehmstedt-Tanasescu reaction is a method in organic chemistry for the organic synthesis of acridone derivatives from a 2-nitrobenzaldehyde and an arene compound :...
- Leimgruber-Batcho indole synthesisLeimgruber-Batcho indole synthesisThe Leimgruber–Batcho indole synthesis is a series of organic reactions that produce indoles from o-nitrotoluenes 1. The first step is the formation of an enamine 2 using N,N-dimethylformamide dimethyl acetal and pyrrolidine...
- Letts nitrile synthesisLetts nitrile synthesisThe Letts nitrile synthesis is the chemical reaction of aromatic carboxylic acids with metal thiocyanates to form nitriles.-References:# Letts, E. A. Ber. 1872, 5, 669.# Mowry, D. T. Chem. Rev. 1948, 42, 264....
- Leuckart reactionLeuckart reactionThe Leuckart reaction is the chemical reaction of ammonium salts of formic acid with aldehydes to form amines by reductive amination. The reaction is named after Rudolf Leuckart....
- Leuckart thiophenol reaction
- Leuckart-Wallach reaction
- Leuckart amide synthesisAmideIn chemistry, an amide is an organic compound that contains the functional group consisting of a carbonyl group linked to a nitrogen atom . The term refers both to a class of compounds and a functional group within those compounds. The term amide also refers to deprotonated form of ammonia or an...
- Levinstein process
- Ley oxidation
- Lieben iodoform reaction, Haloform reactionHaloform reactionThe haloform reaction is a chemical reaction where a haloform is produced by the exhaustive halogenation of a methyl ketone in the presence of a base. R may be , alkyl or aryl...
- Liebeskind–Srogl coupling
- Liebig melamine synthesisMelamineMelamine is an organic base and a trimer of cyanamide, with a 1,3,5-triazine skeleton. Like cyanamide, it contains 66% nitrogen by mass and, if mixed with resins, has fire retardant properties due to its release of nitrogen gas when burned or charred, and has several other industrial uses....
- Lindlar catalystLindlar catalystA Lindlar catalyst is a heterogeneous catalyst that consists of palladium deposited on calcium carbonate and treated with various forms of lead. The lead additive serves to deactivate the palladium sites. A variety of "catalyst poisons" have been used including lead acetate and lead oxide. The...
- Lobry–de Bruyn–van Ekenstein transformation
- Lossen rearrangementLossen rearrangementThe Lossen rearrangement is the conversion of a hydroxamic acid to an isocyanate via the formation of an O-acyl, sulfonyl, or phosphoryl intermediate hydroxamic acid O-derivative and then conversion to its conjugate base. Here, 4-Toluenesulfonyl chloride is used to form a sulfonyl O-derivative...
- Lucas' reagentLucas' reagentLucas' reagent is a solution of zinc chloride in concentrated hydrochloric acid. This solution is used to classify alcohols of low molecular weight. The reaction is a substitution in which the chloride replaces a hydroxyl group. A positive test is indicated by a change from colourless to turbid,...
- Luche reductionLuche reductionLuche reduction is the selective organic reduction of ketones to alcohols with lanthanoid chlorides such as cerium chloride and sodium borohydride. The Luche reduction can be conducted chemoselectively toward ketone in the presence of aldehyde or toward α,β-unsaturated ketone in the presence of...
M
- Maillard reactionMaillard reactionThe Maillard reaction is a form of nonenzymatic browning similar to caramelization. It results from a chemical reaction between an amino acid and a reducing sugar, usually requiring heat....
- Madelung synthesisMadelung synthesisThe Madelung synthesis is a chemical reaction that produces indoles by the intramolecular cyclization of N-phenylamides using strong base at high temperature....
- Malaprade reaction, Periodic acid oxidation
- Malonic ester synthesisMalonic ester synthesisThe malonic ester synthesis is a chemical reaction where diethyl malonate or another ester of malonic acid is alkylated at the carbon alpha to both carbonyl groups, and then converted to a substituted acetic acid. The major drawback of malonic ester synthesis is that the alkylation stage can also...
- Mannich reactionMannich reactionThe Mannich reaction is an organic reaction which consists of an amino alkylation of an acidic proton placed next to a carbonyl functional group with formaldehyde and ammonia or any primary or secondary amine. The final product is a β-amino-carbonyl compound also known as a Mannich base...
- Markó–Lam deoxygenation
- Markovnikov's ruleMarkovnikov's ruleIn organic chemistry, Markovnikov's rule or Markownikoff's rule is an observation based on Zaitsev's rule. It was formulated by the Russian chemist Vladimir Vasilevich Markovnikov in 1870....
, Markownikoff rule, Markownikow rule - Martinet dioxindole synthesisMartinet dioxindole synthesisThe Martinet dioxindole synthesis is a chemical reaction used to synthesize dioxindoles 3 from anilines and esters of mesoxalic acid 1.-Reaction mechanism:...
- McDougall monoprotection
- McFadyen–Stevens reaction
- McMurry reactionMcMurry reactionThe McMurry reaction is an organic reaction in which two ketone or aldehyde groups are coupled to an alkene using titanium chloride compound such as titanium chloride and a reducing agent. The reaction is named after its co-discoverer, John E. McMurry. The McMurry reaction originally involved the...
- Meerwein arylationMeerwein arylationThe Meerwein arylation is an organic reaction involving the addition of an aryl diazonium salt to an electron-poor alkene usually supported by a metal salt. The reaction product is an alkylated arene compound...
- Meerwein–Ponndorf–Verley reduction
- Meisenheimer rearrangement
- Meissenheimer complex
- Menshutkin reactionMenshutkin reactionThe Menshutkin reaction in organic chemistry converts a tertiary amine to a quaternary ammonium salt by reaction with an alkyl halide:The reaction has been named after its discoverer, the Russian chemist Nikolai Menshutkin, who described the procedure in 1890...
- Metal-ion-catalyzed σ-bond rearrangement
- Mesylation
- Merckwald asymmetric synthesis
- MethylationMethylationIn the chemical sciences, methylation denotes the addition of a methyl group to a substrate or the substitution of an atom or group by a methyl group. Methylation is a form of alkylation with, to be specific, a methyl group, rather than a larger carbon chain, replacing a hydrogen atom...
- Meyer and Hartmann reaction
- Meyer reaction
- Meyer synthesis
- Meyer–Schuster rearrangement
- Michael addition
- Michael addition, Michael system
- Michael condensation
- Michaelis–Arbuzov reaction
- Mignonac reaction
- Milas hydroxylationMilas hydroxylationThe Milas hydroxylation is an organic reaction converting an alkene to a vicinal diol, and was developed by N. A. Milas in the 1930s. The cis-diol is formed by reaction of alkenes with hydrogen peroxide and either ultraviolet light or a catalytic osmium, vanadium, or chromium oxide.The reaction...
of olefins - Mitsunobu reactionMitsunobu reactionThe Mitsunobu reaction is an organic reaction that converts an alcohol into a variety of functional groups, such as an ester, using triphenylphosphine and an azodicarboxylate such as diethyl azodicarboxylate or diisopropyl azodicarboxylate . The alcohol undergoes an inversion of stereochemistry...
- Molisch's testMolisch's testMolisch's Test is a sensitive chemical test for the presence of carbohydrates, based on the dehydration of the carbohydrate by sulfuric acid to produce an aldehyde, which condenses with two molecules of phenol Molisch's Test (named after Austrian botanist Hans Molisch) is a sensitive chemical test...
- Mukaiyama aldol additionMukaiyama aldol additionThe Mukaiyama aldol addition is an organic reaction and a type of aldol reaction between a silyl enol ether and an aldehyde catalyzed by a Lewis acid. This choice of reactants allows for a crossed aldol reaction between an aldehyde and a ketone or a different aldehyde without self-condensation of...
- Mukaiyama reaction
- Myers' asymmetric alkylation
N
- Nametkin rearrangement
- Nazarov cyclization reactionNazarov cyclization reactionThe Nazarov cyclization reaction is a chemical reaction used in organic chemistry for the synthesis of cyclopentenones. The reaction is typically divided into classical and modern variants, depending on the reagents and substrates employed...
- Neber rearrangementNeber rearrangementThe Neber rearrangement is an organic reaction in which an oxime is converted into an alpha-aminoketone in a rearrangement reaction.The oxime is first converted to a ketoxime tosylate by reaction with tosyl chloride...
- Nef reactionNef reactionThe Nef reaction is an organic reaction describing the acid hydrolysis of a salt of a primary or secondary nitroalkane to an aldehyde or a ketone and nitrous oxide ....
- Negishi couplingNegishi couplingThe Negishi coupling is a cross coupling reaction in organic chemistry involving an organozinc compound, an organic halide and a nickel or palladium catalyst creating a new carbon-carbon covalent bond:* The halide X can be chloride, bromine or iodine but also a triflate or acetyloxy group with as...
- Negishi-Zipper reaction
- Nenitzescu indole synthesisNenitzescu indole synthesisThe Nenitzescu indole synthesis is a chemical reaction that forms 5-hydroxyindole derivatives from benzoquinone and β-aminocrotonic esters.-References:*Nenitzescu, C. D. Bull. Soc. Chim. Romania 1929, 11, 37....
- Nenitzescu reductive acylation
- Nicholas reactionNicholas reactionThe Nicholas reaction is an organic reaction where a dicobalt octacarbonyl-stabilized propargylic cation is reacted with a nucleophile. Oxidative demetallation gives the desired alkylated alkyne.Several reviews have been published.-Reaction mechanism:...
- Niementowski quinazoline synthesisNiementowski quinazoline synthesisThe Niementowski quinazoline synthesis is the chemical reaction of anthranilic acids with amides to form 4-oxo-3,4-dihydroquinazolines.-References:# Stefan Niementowski, v. J. Prakt. Chem. 1895, 51, 564....
- Niementowski quinoline synthesisNiementowski quinoline synthesisThe Niementowski quinoline synthesis is the chemical reaction of anthranilic acids and ketones to form γ-hydroxyquinoline derivatives.Several reviews have been published.-See also:* Camps quinoline synthesis* Friedländer synthesis...
- Nierenstein reactionNierenstein reactionThe Nierenstein reaction is an organic reaction describing the conversion of an acid chloride into an haloketone with diazomethane. It is an insertion reaction in that the methylene from the diazomethane is inserted into the carbon-chlorine bond of the acid chloride.-Reaction mechanism:Like the...
- NIH shiftNIH shiftAn NIH shift is a chemical rearrangement where a hydrogen atom on an aromatic ring undergoes an intramolecular migration primarily during a hydroxylation reaction. This process is also known as a 1,2-hydride shift. These shifts are often studied and observed by isotopic labeling...
- Ninhydrin testNinhydrinNinhydrin is a chemical used to detect ammonia or primary and secondary amines. When reacting with these free amines, a deep blue or purple color known as Ruhemann's purple is produced...
- Nitroaldol reactionNitroaldol reactionThe Henry Reaction is a classic carbon–carbon bond formation reaction in organic chemistry. Discovered in 1895 by L. Henry, it is the combination of a nitroalkane and an aldehyde or ketone in the presence of a base to form β-Nitro alcohols...
- Nitrone-olefin 3+2 cycloadditionNitrone-olefin 3+2 cycloadditionThe nitrone-olefin [3+2] cycloaddition reaction is the combination of a nitrone with an alkene or alkyne to generate an isoxazoline or isoxazolidine via a [3+2] cycloaddition process.-Introduction:...
- Normant reagents
- Noyori asymmetric hydrogenationNoyori asymmetric hydrogenationThe Noyori asymmetric hydrogenation is a chemical reaction described as an asymmetric reduction of β-keto-esters.Both enantiomers of BINAP are commercially available and widely used...
- Nozaki–Hiyama–Kishi nickel/chromium coupling reaction
- Nucleophilic acyl substitutionNucleophilic acyl substitutionNucleophilic acyl substitution describes the substitution reaction involving nucleophiles and acyl compounds. Acyl compounds are carboxylic acid derivatives including esters, amides and acid halides...
O
- Ohira–Bestmann reaction
- Olah reagentOlah reagentThe Olah reagent is a nucleophilic fluorinating agent. It consists of a mixture of 70% hydrogen fluoride and 30% pyridine; alcohols react with this reagent to give alkyl fluorides:...
- Olefin metathesisOlefin metathesisOlefin metathesis or transalkylidenation is an organic reaction that entails redistribution of alkylene fragments by the scission of carbon - carbon double bonds in olefins . Its advantages include the creation of fewer sideproducts and hazardous wastes. Yves Chauvin, Robert H. Grubbs, and Richard R...
- Oppenauer oxidationOppenauer oxidationOppenauer oxidation, named after Rupert Viktor Oppenauer, is a gentle method for selectively oxidizing secondary alcohols to ketones.The reaction is the opposite of Meerwein-Ponndorf-Verley reduction. The alcohol is oxidized with aluminium isopropoxide in excess acetone...
- Ostromyslenskii reaction, Ostromisslenskii reaction
- Oxidative decarboxylation
- Oxo synthesis
- Oxy-Cope rearrangement
- Oxymercuration
- Oxidation of secondary alcohols to ketonesOxidation of secondary alcohols to ketonesThe oxidation of secondary alcohols to ketones is an important oxidation reaction in organic chemistry.When a secondary alcohol is oxidised, it is converted to a ketone. The hydrogen from the hydroxyl group is lost along with the hydrogen bonded to the second carbon. The remaining oxygen then...
- OzonolysisOzonolysisOzonolysis is the cleavage of an alkene or alkyne with ozone to form organic compounds in which the multiple carbon–carbon bond has been replaced by a double bond to oxygen...
P
- Paal-Knorr pyrrole synthesis
- Paal-Knorr synthesisPaal-Knorr synthesisThe Paal–Knorr Synthesis in organic chemistry is a reaction that generates either furans, pyrroles, or thiophenes from 1,4-diketones. It is a synthetically valuable method for obtaining substituted furans and pyrroles, common structural components of many natural products...
- Paneth technique
- Passerini reactionPasserini reactionThe Passerini reaction is a chemical reaction involving an isocyanide, an aldehyde , and a carboxylic acid to form a α-acyloxy amide. This organic reaction was discovered by Mario Passerini in 1921 in Florence, Italy...
- Paternò–Büchi reaction
- Pauson-Khand reaction
- Payne rearrangementPayne rearrangementThe Payne rearrangement is the isomerization, under basic conditions, of 2,3-epoxy alcohols to isomeric 2,3-epoxy alcohols with inversion of configuration...
- Pechmann condensationPechmann condensationThe Pechmann condensation is a synthesis of coumarins, starting from a phenol and a carboxylic acid or ester containing a β-carbonyl group . The condensation is performed under acidic conditions. The mechanism involves an esterification/transesterification followed by attack of the activated...
- Pechmann pyrazole synthesis
- Pellizzari reactionPellizzari reactionThe Pellizzari reaction is the chemical reaction of an amide and a hydrazide to form a 1,2,4-triazole....
- Pelouze synthesis
- Peptide synthesisPeptide synthesisIn organic chemistry, peptide synthesis is the production of peptides, which are organic compounds in which multiple amino acids are linked via amide bonds which are also known as peptide bonds...
- Perkin alicyclic synthesis
- Perkin reactionPerkin reactionThe Perkin reaction is an organic reaction developed by William Henry Perkin that can be used to make cinnamic acids i.e. α-β-unsaturated aromatic acid by the aldol condensation of aromatic aldehydes and acid anhydrides in the presence of an alkali salt of the acid.Several reviews have been written....
- Perkin rearrangement
- Perkow reactionPerkow reactionThe Perkow reaction is an organic reaction in which a trialkyl phosphite ester reacts with a haloketone to form a dialkyl vinyl phosphate and an alkyl halide....
- Petasis reactionPetasis reactionThe Petasis reaction is the chemical reaction of an amine, aldehyde, and vinyl- or aryl-boronic acid to form substituted amines.Reported in 1993 by N.A. Petasis as a practical method towards the synthesis of a geometrically pure antifungal agent, naftifine, the Petasis reaction can be described as...
- Petasis reagentPetasis reagentThe Petasis reagent is dimethyl titanocene, Cp2TiMe2, readily prepared by the reaction of methylmagnesium chloride or methyllithium with titanocene dichloride:...
- Peterson olefinationPeterson olefinationThe Peterson olefination is the chemical reaction of α-silyl carbanions 1 with ketones to form a β-hydroxysilane 2 which eliminates to form alkenes 3.Several reviews have been published....
- Peterson reaction
- Petrenko-Kritschenko piperidone synthesisPetrenko-Kritschenko piperidone synthesisThe Petrenko-Kritschenko reaction is a classic multicomponent name reaction that is closely related to the Robinson-Schöpf tropinone synthesis, but was published 12 years earlier.-Classic reaction:...
- Pfau-Plattner azulene synthesis
- Pfitzinger reactionPfitzinger reactionThe Pfitzinger reaction is the chemical reaction of isatin with base and a carbonyl compound to yield substituted quinoline-4-carboxylic acids.Several reviews have been published.-Reaction mechanism:...
- Pfitzner-Moffatt oxidationPfitzner-Moffatt oxidationThe Pfitzner–Moffatt oxidation, sometimes referred to as simply the Moffatt oxidation, is a chemical reaction which describes the oxidation of primary and secondary alcohols by dimethyl sulfoxide activated with a carbodiimide, such as dicyclohexylcarbodiimide...
- Piancatelli rearrangementPiancatelli rearrangementIn 1976, The Italian chemist G. Piancatelli and co-workers develop a new method to synthesize the 4-hydroxycyclopentenone derivatives from suitable 2-furylcarbinols through an acid-catalyzed rearrangement ....
- Pictet-Gams isoquinoline synthesis
- Pictet-Hubert reaction
- Pictet-Spengler tetrahydroisoquinoline synthesis
- Pictet-Spengler reactionPictet-Spengler reactionThe Pictet–Spengler reaction is a chemical reaction in which a β-arylethylamine such as tryptamine undergoes ringclosure after condensation with an aldehyde or ketone. Usually an acidic catalyst is employed and the reaction mixture heated, but some reactive compounds give good yields even at...
- Piloty-Robinson pyrrole synthesis
- Pinacol coupling reactionPinacol coupling reactionA pinacol coupling reaction is an organic reaction in which a carbon–carbon covalent bond is formed between the carbonyl groups of an aldehyde or a ketone in presence of an electron donor in a free radical process . The reaction product is a vicinal diol...
- Pinacol rearrangementPinacol rearrangementThe pinacol rearrangement or pinacol-pinacolone rearrangement is a method for converting a 1,2-diol to a carbonyl compound in organic chemistry. This 1,2-rearrangement takes place under acidic conditions...
- Pinner amidine synthesis
- Pinner method for ortho esters
- Pinner reactionPinner reactionThe Pinner reaction is an organic reaction of a nitrile with an alcohol under acid catalysis for instance hydrochloric acid. The product formed is the hydrochloric acid salt of an imino ester or an alkyl imidate, which sometimes is called a Pinner salt...
- Pinner triazine synthesis
- Piria reaction
- Pitzer strain
- Polonovski reaction
- Pomeranz-Fritsch reaction
- Ponzio reaction
- Prelog strainPrelog strainthumb|right|Cyclodecane in its lowest energy conformation. The red triangle indicates three hydrogens responsible for transannular strain. There is an identical interaction on the back of the molecule, as well. In organic chemistry, transannular strain is the unfavorable interactions of ring...
- Prevost reactionPrévost reactionThe Prévost reaction is chemical reaction in which an alkene is converted by iodine and the silver salt of benzoic acid to a vicinal diol with anti stereochemistry...
- Prileschajew reaction
- Prilezhaev reaction
- Prins reactionPrins reactionThe Prins reaction is an organic reaction consisting of an electrophilic addition of an aldehyde or ketone to an alkene or alkyne followed by capture of a nucleophile. The outcome of the reaction depends on reaction conditions . With water and a protic acid such as sulfuric acid as the reaction...
- Prinzbach synthesis
- Protecting groupProtecting groupA protecting group or protective group is introduced into a molecule by chemical modification of a functional group in order to obtain chemoselectivity in a subsequent chemical reaction...
- Pschorr reaction
- Pummerer rearrangementPummerer rearrangementThe Pummerer rearrangement is an organic reaction whereby an alkyl sulfoxide rearranges to an α-acyloxy–thioether in the presence of acetic anhydride. In this reaction, sulfur is reduced while adjacent carbon is oxidized....
- Purdie methylation, Irvine-Purdie methylation
R
- Ramberg-Backlund reactionRamberg-Bäcklund reactionThe Ramberg-Bäcklund Reaction is an organic reaction converting an α-halo sulfone into an alkene in presence of a base with extrusion of sulfur dioxide. The reaction is named after the two Swedish chemists Ludwig Ramberg and Birger Bäcklund. The carbanion formed by deprotonation gives an unstable...
- Raney-Nickel
- Rap-Stoermer condensation
- Raschig phenol process
- Rauhut–Currier reaction
- RacemizationRacemizationIn chemistry, racemization refers to the converting of an enantiomerically pure mixture into a mixture where more than one of the enantiomers are present...
- Reductive aminationReductive aminationReductive amination is a form of amination that involves the conversion of a carbonyl group to an amine via an intermediate imine...
- Reductive dehalogenation of halo ketonesReductive dehalogenation of halo ketonesReductive dehalogenations of halo ketones are organic reactions that result in the formation of ketones and functionalized derivatives of ketones from α-halo ketones in the presence of metallic reducing agents.-Introduction:...
- Reed reactionReed reactionThe Reed reaction is a chemical reaction that utilizes light to oxidize hydrocarbons to sulfonyl chlorides. The reaction performs via the free radicals. First, the light makes a molecule of chlorine dissociate homolytically, then an chlorine atom produced attacks the hydrocarbon chain to form...
- Reformatskii reactionReformatskii reactionThe Reformatsky reaction is an organic reaction which condenses aldehydes , 1, with α-halo esters, 2, using a metallic zinc to form β-hydroxy-esters, 3...
- Reilly-Hickinbottom rearrangement
- Reimer-Tiemann reactionReimer-Tiemann reactionThe Reimer-Tiemann reaction is a chemical reaction used for the ortho-formylation of phenols. The reaction was discovered by Karl Ludwig Reimer and Ferdinand Tiemann...
- Reissert indole synthesisReissert indole synthesisThe Reissert indole synthesis is a series of chemical reactions designed to synthesize indole or substituted-indoles from ortho-nitrotoluene 1 and diethyl oxalate 2....
- Reissert reactionReissert reactionThe Reissert reaction is a series of chemical reactions that transforms quinoline to quinaldic acid. Quinolines will react with acid chlorides and potassium cyanide to give 1-acyl-2-cyano-1,2-dihydroquinolines, also known as Reissert compounds...
, Reissert compound - Reppe synthesis
- Retropinacol rearrangement
- Rieche formylationRieche formylationRieche formylation is a type of formylation reaction . The substrates are sterically hindered aromatic compounds - for example mesitylene - and the formylation reagent dichloromethyl methyl ether. The catalyst is titanium tetrachloride, the workup is acidic. The reaction is named after Alfred...
- Riemschneider thiocarbamate synthesisRiemschneider thiocarbamate synthesisThe Riemschneider thiocarbamate synthesis produces aromatic thiocarbamates starting with the corresponding aromatic thiocyanate.500px|centerThe thiocyanate is treated with sulfuric acid and then hydrolyzed with ice water....
- Riley oxidations
- Rothemund synthesisPorphyrinPorphyrins are a group of organic compounds, many naturally occurring. One of the best-known porphyrins is heme, the pigment in red blood cells; heme is a cofactor of the protein hemoglobin. Porphyrins are heterocyclic macrocycles composed of four modified pyrrole subunits interconnected at...
- Ring closing metathesisOlefin metathesisOlefin metathesis or transalkylidenation is an organic reaction that entails redistribution of alkylene fragments by the scission of carbon - carbon double bonds in olefins . Its advantages include the creation of fewer sideproducts and hazardous wastes. Yves Chauvin, Robert H. Grubbs, and Richard R...
- Ring opening metathesisOlefin metathesisOlefin metathesis or transalkylidenation is an organic reaction that entails redistribution of alkylene fragments by the scission of carbon - carbon double bonds in olefins . Its advantages include the creation of fewer sideproducts and hazardous wastes. Yves Chauvin, Robert H. Grubbs, and Richard R...
- Ritter reactionRitter reactionThe Ritter reaction is a chemical reaction that transforms a nitrile into a N-alkyl amide using various alkylating reagents, for example, strong acid and isobutylene....
- Robinson annulationRobinson annulationThe Robinson annulation is an organic reaction used to create a six-member ring α,β-unsaturated cyclic ketone, using a ketone and methyl vinyl ketone...
- Robinson-Gabriel synthesisRobinson-Gabriel synthesisThe Robinson-Gabriel synthesis is a chemical reaction that forms oxazoles by dehydration of 2-acylamino-ketones.Historically, the dehydration agent is concentrated sulfuric acid. Recently, phosphorus oxychloride is successful with this reaction also....
- Robinson Schopf reaction
- Rosenmund reaction
- Rosenmund reductionRosenmund reductionThe Rosenmund reduction is a chemical reaction that reduces an acid halide to an aldehyde using hydrogen gas over palladium-on-carbon poisoned with barium sulfate...
- Rosenmund-von Braun synthesisRosenmund-von Braun synthesisThe Rosenmund-von Braun synthesis is an organic reaction in which an aryl halide reacts with cuprous cyanide to an aryl nitrile..The reaction was named after Karl Wilhelm Rosenmund who together with his Ph.D. student Erich Struck discovered in 1914 that aryl halide reacts with alcohol water...
- Rothemund reaction
- Rupe rearrangement
- Rubottom oxidationRubottom oxidationThe Rubottom oxidation is the chemical reaction of enolsilanes with m-chloroperoxybenzoic acid to give silyl-protected α-hydroxy ketones.-Reaction mechanism:...
- Ruff-Fenton degradation
- Ruzicka large ring synthesisRuzicka large ring synthesisThe Ruzicka large ring synthesis or Ruzicka reaction or Ruzicka cyclization is an organic reaction in which a dicarboxylic acid is converted to a cyclic ketone at high temperature and a suitable catalyst such as thorium oxide...
S
- Sakurai reactionSakurai reactionThe Sakurai reaction is the chemical reaction of carbon electrophiles with allylic silanes catalyzed by strong Lewis acids. It is named after the chemists Akira Hosomi and Hideki Sakurai.Lewis acid activation is essential for complete reaction...
- Salol reaction
- Sandheimer
- Sandmeyer diphenylurea isatin synthesis
- Sandmeyer isonitrosoacetanilide isatin synthesis
- Sandmeyer reactionSandmeyer reactionThe Sandmeyer reaction is a chemical reaction used to synthesize aryl halides from aryl diazonium salts. It is named after the Swiss chemist Traugott Sandmeyer....
- Sanger reagent
- SaponificationSaponificationSaponification is a process that produces soap, usually from fats and lye. In technical terms, saponification involves base hydrolysis of triglycerides, which are esters of fatty acids, to form the sodium salt of a carboxylate. In addition to soap, such traditional saponification processes...
- Sarett oxidationSarett oxidationThe Sarett oxidation is the oxidation of an alcohol to a ketone or an aldehyde using chromium trioxide and pyridine. Primary alcohols will only be oxidised to the aldehyde and not on to carboxylic acids....
- Saytzeff rule, Saytzeff's Rule
- Schiemann reactionSchiemann reactionThe Schiemann reaction is a chemical reaction in which anilines are transformed to aryl fluorides via diazonium fluoroborates...
- Schiff reactionSchiff baseA Schiff base, named after Hugo Schiff, is a compound with a functional group that contains a carbon-nitrogen double bond with the nitrogen atom connected to an aryl or alkyl group, not hydrogen....
- Schiff testSchiff testThe Schiff test invented and named after Hugo Schiff is a chemical test for the detection of aldehydes. An unknown sample is added to the decolorized Schiff reagent and when aldehyde is present a characteristic magenta or purple color develops. The Schiff reagent is the reaction product of...
- Schlenk equilibriumSchlenk equilibriumThe Schlenk equilibrium is a chemical equilibrium named after its discoverer Wilhelm Schlenk taking place in solutions of Grignard reagents.The process described is an equilibrium between two equivalents of an alkyl or aryl magnesium halide on the left of the equation and on the right side, one...
- Schlosser modification
- Schlosser variant
- Schmidlin ketene synthesis
- Schmidt degradation
- Schmidt reactionSchmidt reactionThe Schmidt reaction is an organic reaction involving alkyl migration over the carbon-nitrogen chemical bond in an azide with expulsion of nitrogen...
- Scholl reactionScholl reactionThe Scholl reaction is a coupling reaction between two arene compounds with the aid of a Lewis acid and a protic acid. It is named after its discoverer, Roland Scholl....
- Schorigin Shorygin reaction, Shorygin reaction, Wanklyn reaction
- Schotten-Baumann reactionSchotten-Baumann reactionThe Schotten-Baumann reaction is a method to synthesise amides from amines and acid chlorides:Sometimes the name for this reaction is also used to indicate the reaction between an acid chloride and a alcohol to form an ester...
- Seliwanoff's testSeliwanoff's testSeliwanoff’s test is a chemical test which distinguishes between aldose and ketose sugars. Ketoses are distinguished from aldoses via their ketone/aldehyde functionality. If the sugar contains a ketone group, it is a ketose and if it contains an aldehyde group, it is an aldose...
- Semidine rearrangement
- Semmler-Wolff reaction
- Seyferth-Gilbert homologationSeyferth-Gilbert homologationThe Seyferth–Gilbert homologation is a the chemical reaction of an aryl ketone 1 with dimethyl phosphonate 2 and potassium tert-butoxide to give substituted alkynes 3...
- Shapiro reactionShapiro reactionThe Shapiro reaction or tosylhydrazone decomposition is an organic reaction in which a ketone or aldehyde is converted to an alkene through an intermediate hydrazone in the presence of 2 equivalents of strong base. The reaction was discovered by Robert H. Shapiro in 1975...
- Sharpless asymmetric dihydroxylationSharpless asymmetric dihydroxylationSharpless asymmetric dihydroxylation is the chemical reaction of an alkene with osmium tetroxide in the presence of a chiral quinine ligand to form a vicinal diol....
- Sharpless epoxidationSharpless epoxidationThe Sharpless Epoxidation reaction is an enantioselective chemical reaction to prepare 2,3-epoxyalcohols from primary and secondary allylic alcohols....
- Sharpless oxyaminationSharpless oxyaminationThe Sharpless oxyamination is the chemical reaction of alkenes with alkyl imido osmium compounds to form vicinal amino-alcohols. A comprehensive review of this reaction was authored by McLeod et al. in 2002.Vicinal amino-alcohols are important products in organic synthesis and recurring...
or aminohydroxylation - Shenck ene reactionEne reactionThe Ene reaction is a chemical reaction between an alkene with an allylic hydrogen and a compound containing a multiple bond , in order to form a new σ-bond with migration of the ene double bond and 1,5 hydrogen shift. The product is a substituted alkene with the double bond shifted to the...
- Sigmatropic reactionSigmatropic reactionA sigmatropic reaction in organic chemistry is a pericyclic reaction wherein the net result is one σ-bond is changed to another σ-bond in an uncatalyzed intramolecular process. The name sigmatropic is the result of a compounding of the long-established sigma designation from single carbon-carbon...
- Simmons-Smith reactionSimmons-Smith reactionThe Simmons–Smith reaction is an organic cheletropic reaction in which a carbenoid reacts with an alkene to form a cyclopropane. It is named after Howard Ensign Simmons, Jr. and R. D. Smith...
- Simonini reaction
- Simonis chromone cyclization
- Simons processElectrochemical fluorinationElectrochemical fluorination , or electrofluorination, is a foundational organofluorine chemistry method for the preparation of fluorocarbon-based organofluorine compounds. The general approach represents an application of electrosynthesis...
- Skraup chinolin synthesis
- Skraup reactionSkraup reactionThe Skraup synthesis is a chemical reaction used to synthesize quinolines. It is named after the Czech chemist Zdenko Hans Skraup . In the archetypal Skraup, aniline is heated with sulfuric acid, glycerol, and an oxidizing agent, like nitrobenzene to yield quinoline.In this example, nitrobenzene...
- Smiles rearrangementSmiles rearrangementThe Smiles rearrangement is an organic reaction and a rearrangement reaction. It is an intramolecular nucleophilic aromatic substitution of the type:...
- SNAr nucleophilic aromatic substitution
- SN1
- SN2
- SNiSNiSNi or Substitution Nucleophilic internal stands for a specific but not often encountered nucleophilic aliphatic substitution reaction mechanism. The name was introduced by Cowdrey et al...
- SolvolysisSolvolysisSolvolysis is a special type of nucleophilic substitution or elimination where the nucleophile is a solvent molecule. For certain nucleophiles, there are specific terms for the type of solvolysis reaction...
- Sommelet reactionSommelet reactionThe Sommelet reaction is an organic reaction in which a benzyl halide is converted to an aldehyde by action of hexamine and water..The reaction is formally an oxidation of the carbon...
- Sonn-Müller method
- Sonogashira couplingSonogashira couplingIn organic chemistry, a Sonogashira coupling is a coupling reaction of terminal alkynes with aryl or vinyl halides. This reaction was first reported by Kenkichi Sonogashira and Nobue Hagihara in 1975.-Catalyst:...
- Sørensen formol titrationSørensen formol titrationThe Sørensen formol titration invented by S. P. L. Sørensen in 1907 is a titration of an amino acid with formaldehyde in the presence of potassium hydroxide....
- Staedel-Rugheimer pyrazine synthesis
- Staudinger reactionStaudinger reactionThe Staudinger reaction or Staudinger reduction is a chemical reaction in which the combination of an azide with a phosphine or phosphite produces an iminophosphorane intermediate. Combined with the hydrolysis of the aza-ylide to produce a phosphine oxide and an amine, this reaction is a mild...
- Stephen aldehyde synthesisStephen aldehyde synthesisStephen aldehyde synthesis, a named reaction in chemistry, was invented by Henry Stephen . This reaction involves the preparation of aldehydes from nitriles using tin chloride , hydrochloric acid and quenching the resulting iminium salt with water .Overall, the reaction scheme is as...
- Stetter reactionStetter reactionThe Stetter reaction is an organic reaction involving the nucleophile catalyzed conjugate addition of an aldehyde to a Michael acceptor such as an enone. The reaction product is a 1,4-dicarbonyl compound...
- Stevens rearrangementStevens rearrangementThe Stevens rearrangement in organic chemistry is an organic reaction converting quaternary ammonium salts and sulfonium salts to the corresponding amines or sulfides in presence of a strong base in a 1,2-rearrangement....
- Stieglitz rearrangementStieglitz rearrangementThe Stieglitz rearrangement is a rearrangement reaction of a trityl hydroxylamine Ar3CNHOH to a triaryl imine . The reaction is related to the Beckmann rearrangement as both reaction involve a carbon to nitrogen shift....
- Stille coupling
- Stobbe condensation
- Stollé synthesisStollé synthesisThe Stollé synthesis is a series of chemical reactions that produce oxindoles from anilines and α-haloacid chlorides . The first step is an amide coupling, while the second step is a Friedel-Crafts reaction. An improved procedure has been developed....
- Stork acylation
- Stork enamine alkylationStork enamine alkylationStork enamine alkylation, also known as the Stork-Enamine reaction, involves the addition of an enamine to an alpha, beta-unsaturated carbonyl acceptor in a process similar to the Michael reaction...
- Strecker amino acid synthesisStrecker amino acid synthesisThe Strecker amino acid synthesis, devised by Adolph Strecker, is a series of chemical reactions that synthesize an amino acid from an aldehyde . The aldehyde is condensed with ammonium chloride in the presence of potassium cyanide to form an α-aminonitrile, which is subsequently hydrolyzed to give...
- Strecker degradationStrecker degradationThe Strecker degradation is a chemical reaction which converts an α-amino acid into an aldehyde by an imine intermediate. It is named after Adolph Strecker, a German chemist.The original observation by Strecker involved the use of alloxan as the oxidant:...
- Strecker sulfite alkylation
- Strecker synthesis
- Suzuki coupling
- Swain equation
- Swarts reaction
- Swern oxidationSwern oxidationThe Swern oxidation, named after Daniel Swern, is a chemical reaction whereby a primary or secondary alcohol is oxidized to an aldehyde or ketone using oxalyl chloride, dimethyl sulfoxide and an organic base, such as triethylamine...
T
- Tamao oxidation
- Tafel rearrangement
- Takai olefinationTakai olefinationTakai olefination in organic chemistry describes the organic reaction of an aldehyde with a diorganochromium compound to form an alkene. In the original 1986 publication the aldehyde is benzaldehyde and the organochromium species is generated from iodoform or bromoform and an excess of chromium...
- Tebbe olefination
- ter Meer reaction
- Thiele reaction
- Thiol-yne reactionThiol-yne reactionThe Thiol-yne reaction is an organic reaction between a thiol and an alkyne. The reaction product is an alkenyl sulfide...
- Thorpe reactionThorpe reactionThe Thorpe reaction is a chemical reaction described as a self-condensation of aliphatic nitriles catalyzed by base to form enamines. The reaction was discovered by Jocelyn Field Thorpe.-Thorpe–Ziegler reaction:...
- Tiemann rearrangement
- Tiffeneau ring enlargement reaction
- Tiffeneau-Demjanow rearrangement
- Tischtschenko reaction
- Tishchenko reactionTishchenko reactionThe Tishchenko reaction is a chemical reaction that involves disproportionation of an aldehyde lacking a hydrogen atom in the alpha position in the presence of an alkoxide. The reaction product is an ester. Catalysts are aluminium alkoxides or sodium alkoxides...
, Tischischenko-Claisen reaction - Tollens reagent
- Transfer hydrogenationTransfer hydrogenationTransfer hydrogenation is the addition of hydrogen to a molecule from a source other than gaseous H2. It is applied in industry and in organic synthesis, in part because of the inconvenience and expense of using gaseous H2...
- Trapp mixtureTrapp mixtureThe Trapp mixture is a specific mixture of organic solvents for chemical reactions taking place at very low temperatures. The mixture THF:diethyl ether: pentane is a liquid down to -110 °C and the same mixture is liquid down to −120 °C. Note that pure THF melts at −108.4 °C.- References :#...
- TransesterificationTransesterificationIn organic chemistry, transesterification is the process of exchanging the organic group R″ of an ester with the organic group R′ of an alcohol. These reactions are often catalyzed by the addition of an acid or base catalyst...
- Traube purine synthesis
- Truce-Smiles rearrangement
- Tscherniac-Einhorn reaction
- Tschitschibabin reaction
- Tschugajeff reaction
- Twitchell process
- Tyrer sulfonation process
U
- Ugi reactionUgi reactionThe Ugi reaction is a multi-component reaction in organic chemistry involving a ketone or aldehyde, an amine, an isocyanide and a carboxylic acid to form a bis-amide.The reaction is named after Ivar Karl Ugi, who first published this reaction in 1959....
- Ullmann reactionUllmann reactionThe Ullmann reaction or Ullmann coupling is a coupling reaction between aryl halides with copper. The reaction is named after Fritz Ullmann....
- Upjohn dihydroxylationUpjohn dihydroxylationUpjohn dihydroxylation is an organic reaction converting an alkene to a cis vicinal diol, and was developed by V. VanRheenen, R. C. Kelly and D. Y. Cha of the Upjohn Company, USA in 1976...
- Urech cyanohydrin method
- Urech hydantoin synthesisUrech hydantoin synthesisThe Urech hydantoin synthesis is the chemical reaction of amino acids with potassium cyanate and hydrochloric acid to give hydantoins....
V
- Van Slyke determinationVan Slyke determinationThe Van Slyke determination is a chemical test for the determination of amino acids containing a primary amine group. A sample is brought into contact with a solution of sodium nitrite in glycerol, water and acetic acid. The resulting diazotisation reaction produces nitrogen gas which can be...
- Varrentrapp reactionVarrentrapp reactionThe Varrentrapp reaction is an organic reaction involving the chemical decomposition of an α,β-unsaturated acid into two other acid fragments by action of molten alkali. This reaction pioneered by F...
- Vilsmeier reaction
- Vilsmeier-Haack reactionVilsmeier-Haack reactionThe Vilsmeier–Haack reaction is the chemical reaction of a substituted amide with phosphorus oxychloride and an electron-rich arene to produce an aryl aldehyde or ketone . The reaction is named after Anton Vilsmeier and Albrecht Haack...
- Voight amination
- Volhard-Erdmann cyclizationVolhard-Erdmann cyclizationThe Volhard-Erdmann cyclization is an organic synthesis of alkyl and aryl thiophenes by cyclization of disodium succinate or other 1,4-difunctional compounds with phosphorus heptasulfide.The reaction is named after Jacob Volhard and Hugo Erdmann.An example is the synthesis of 3-methylthiophene...
- von Braun amide degradationVon Braun amide degradationThe Von Braun amide degradation is the chemical reaction of a monosubstituted amide with phosphorus pentachloride to give a nitrile and an organohalide....
- von Braun reactionVon Braun reactionThe Von Braun reaction is an organic reaction in which a tertiary amine reacts with cyanogen bromide to an organocyanamide. An example is the reaction of dimethyl-α-naphthylamine :...
- von Richter cinnoline synthesis
- von Richter reactionVon Richter reactionThe von Richter reaction is the chemical reaction of aromatic nitro compounds with potassium cyanide giving carboxylation ortho to the position of the former nitro group. The reaction is named after Victor von Richter.-Reaction mechanism:...
W
- Wacker-Tsuji oxidation
- Wagner-Jauregg reactionWagner-Jauregg reactionThe Wagner-Jauregg reaction is a classic organic reaction in organic chemistry, named after Theodor Wagner-Jauregg, describing the double Diels–Alder reaction of 2 equivalents of maleic anhydride with a 1,1-diarylethylene...
- Wagner-Meerwein rearrangementWagner-Meerwein rearrangementA Wagner–Meerwein rearrangement is a class of carbocation 1,2-rearrangement reactions in which a hydrogen, alkyl or aryl group migrates from one carbon to a neighboring carbon.Several reviews have been published....
- Walden inversionWalden inversionWalden inversion is the inversion of a chiral center in a molecule in a chemical reaction. Since a molecule can form two enantiomers around a chiral center, the Walden inversion converts the configuration of the molecule from one enantiomeric form to the other. For example, in a SN2 reaction,...
- Wallach rearrangementWallach rearrangementThe Wallach rearrangement, named after Otto Wallach, is an organic reaction and a rearrangement reaction converting an aromatic azoxy compound with sulfuric acid to an azo compound with one arene ring substituted by an hydroxyl group in the aromatic para position.60% to 100% sulfuric acid is...
- Weerman degradationWeerman degradationThe Weerman degradation is an organic reaction in carbohydrate chemistry in which an aldonamide is degraded by sodium hypochlorite, forming a new sugar with one less carbon. The reaction is named after R.A. Weerman...
- Weinreb ketone synthesisWeinreb ketone synthesisThe Weinreb ketone synthesis is a chemical reaction used in organic chemistry to make carbon–carbon bonds. It was discovered in 1981 by Steven M. Weinreb and Steven Nahm as a method to synthesize ketones...
- Wenker ring closure
- Wenker synthesisWenker synthesisThe Wenker synthesis is an organic reaction converting a beta amino alcohol to an aziridine with the aid of sulfuric acid.The original Wenker synthesis of aziridine itself takes place in two steps...
- Wessely-Moser rearrangement
- Westphalen-Lettré rearrangementWestphalen-Lettré rearrangementThe Westphalen–Lettré rearrangement is a classic organic reaction in organic chemistry describing a rearrangement reaction of cholestane-3β,5α,6β-triol diacetate with acetic anhydride and sulfuric acid. In this reaction one equivalent of water is lost, a double bond is formed at C10-C11 and...
- Wharton reactionWharton reactionThe Wharton reaction is the chemical reaction of α,β-epoxy-ketones with hydrazine to give allylic alcohols. It can be used to synthesize carenol compounds.Dupuy has developed an improved procedure.-Reaction mechanism:...
- Whiting reactionWhiting reactionThe Whiting reaction is an organic reaction converting a propargyl diol into a diene using lithium aluminium hydride.This organic reduction has been applied in the synthesis of fecapentaene....
- Wichterle reaction
- Widman-Stoermer synthesis
- Wilkinson catalyst
- Willgerodt rearrangementWillgerodt rearrangementThe Willgerodt rearrangement or Willgerodt reaction is an organic reaction converting an aryl alkyl ketone to the corresponding amide by reaction with ammonium polysulfide, named after Conrad Willgerodt. The formation of the corresponding carboxylic acid is a side reaction...
- Willgerodt-Kindler reaction
- Williamson ether synthesisWilliamson ether synthesisThe Williamson ether synthesis is an organic reaction, forming an ether from an organohalide and an alcohol. This reaction was developed by Alexander Williamson in 1850. Typically it involves the reaction of an alkoxide ion with a primary alkyl halide via an SN2 reaction...
- Winstein reaction
- Wittig reactionWittig reactionThe Wittig reaction is a chemical reaction of an aldehyde or ketone with a triphenyl phosphonium ylide to give an alkene and triphenylphosphine oxide....
- Wittig rearrangement
- Wittig-Horner reaction
- Wohl degradationWohl degradationThe Wohl degradation in carbohydrate chemistry is a chain contraction method for aldoses. The classic example is the conversion of glucose to arabinose as shown below. The reaction is named after the chemist Alfred Wohl....
- Wohl-Aue reactionWohl-Aue reactionThe Wohl-Aue reaction is an organic reaction between an aromatic nitro compound and an aniline to form a phenazine in presence of an alkali base. An example is the reaction between nitrobenzene and aniline:The reaction is named after Alfred Wohl and W. Aue....
- Wohler synthesisWöhler synthesisrightThe Wöhler synthesis is the conversion of ammonium cyanate into urea. This chemical reaction was discovered in 1828 by Friedrich Wöhler in an attempt to synthesize ammonium cyanate. It is considered the starting point of modern organic chemistry. Although the Wöhler reaction concerns the...
- Wohl-Ziegler reactionWohl-Ziegler reactionThe Wohl-Ziegler reactionis a chemical reaction that involves the allylic or benzylic bromination of hydrocarbons using an N-bromoimide and a radical initiator.Best yields are achieved with N-bromosuccinimide in carbon tetrachloride solvent...
- Wolffenstein-Böters reactionWolffenstein-Böters reactionThe Wolffenstein-Böters reaction is an organic reaction converting benzene to picric acid by a mixture of aqueous nitric acid and mercury nitrate....
- Wolff rearrangementWolff rearrangementThe Wolff rearrangement is a rearrangement reaction converting a α-diazo-ketone into a ketene. This reaction was first reported by Ludwig Wolff in 1912....
- Wolff-Kishner reductionWolff-Kishner reductionThe Wolff–Kishner reduction is a chemical reaction that fully reduces a ketone to an alkane.The method originally involved heating the hydrazine with sodium ethoxide in a sealed vessel at about 180 °C. Other bases have been found equally effective...
- Woodward cis-hydroxylationWoodward cis-hydroxylationThe Woodward cis-hydroxylation is the chemical reaction of alkenes with iodine and silver acetate in wet acetic acid to form cis-diols. The reaction is named after its discoverer, Robert Burns Woodward....
- Woodward-Hoffmann rule
- Wulff-Dötz reaction
- Wurtz coupling, Wurtz reactionWurtz reactionThe Wurtz reaction, named after Charles-Adolphe Wurtz, is a coupling reaction in organic chemistry, organometallic chemistry and recently inorganic main group polymers, whereby two alkyl halides are reacted with sodium to form a new carbon-carbon bond:...
- Wurtz-Fittig reactionWurtz-Fittig reactionThe Wurtz-Fittig reaction is the chemical reaction of aryl halides with alkyl halides and sodium metal to give substituted aromatic compounds....
Z
- Zeisel determinationZeisel determinationThe Zeisel determination or Zeisel test is a chemical test for the presence of esters or ethers in a chemical substance. It is named after the Czech chemist Simon Zeisel . In a qualitative test a sample is first reacted with a mixture of acetic acid and hydriodic acid in a test tube...
- Zerevitinov determination, Zerewitinoff determinationZerewitinoff determinationThe Zerewitinoff determination or Zerevitinov determination is a quantitative chemical test for the determination of active hydrogens in a chemical substance. A sample is treated with the Grignard reagent, methylmagnesium iodide, which reacts with any acidic hydrogen atom to form methane. This gas...
- Ziegler condensation
- Ziegler method
- Zimmermann reaction
- Zincke disulfide cleavage
- Zinke nitrationZinke nitrationThe Zincke nitration is an organic reaction in which a bromine substituent of a phenol or cresol is replaced by a nitro group by treatment with nitrous acid or sodium nitrite. The reaction is a manifestation of nucleophilic aromatic substitution...
- Zincke reactionZincke reactionThe Zincke reaction is an organic reaction in which a pyridine is transformed into a pyridinium salt by reaction with 2,4-dinitro-chlorobenzene and a primary amine, named after Theodor Zincke....
- Zincke-Suhl reactionZincke-Suhl reactionThe Zincke-Suhl reaction is a special case of a Friedel-Crafts alkylation and was first described by Theodor Zincke and Suhl.The classic example of this reaction is the conversion of p-cresol to a cyclohexadienone . Melvin Newman, a scientist from the U.S...
- Zinin reduction
See also
- List of organic compounds
- List of inorganic compounds
- Named inorganic compounds
- List of biomolecules
- List of minerals
:Category:Reaction images
External links
- http://www.organic-chemistry.org/namedreactions/
- http://www.synarchive.com/reaction
- http://www.chem.wisc.edu/areas/reich/handouts/NameReagents/namedreag-cont.htm