Thiocarbamate
Encyclopedia
Thiocarbamates are a family of organosulfur compounds. There are two isomeric forms
of thiocarbamate ester
s: O-thiocarbamates, ROC(=S)NR2, and S-thiocarbamates, RSC(=O)NR2. O-thiocarbamates can isomerise
to S-thiocarbamates, for example in the Newman-Kwart rearrangement
.
by hydrolysis
of thiocyanates:
Where R is aryl
, this method is known as the Riemschneider thiocarbamate synthesis
.
Isomer
In 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...
of thiocarbamate ester
Ester
Esters are chemical compounds derived by reacting an oxoacid with a hydroxyl compound such as an alcohol or phenol. Esters are usually derived from an inorganic acid or organic acid in which at least one -OH group is replaced by an -O-alkyl group, and most commonly from carboxylic acids and...
s: O-thiocarbamates, ROC(=S)NR2, and S-thiocarbamates, RSC(=O)NR2. O-thiocarbamates can isomerise
Isomerisation
In chemistry isomerisation is the process by which one molecule is transformed into another molecule which has exactly the same atoms, but the atoms are rearranged e.g. A-B-C → B-A-C . In some molecules and under some conditions, isomerisation occurs spontaneously...
to S-thiocarbamates, for example in the Newman-Kwart rearrangement
Newman-Kwart rearrangement
The Newman–Kwart rearrangement is a type of rearrangement reaction in which the aryl group of an O-aryl thiocarbamate, ArOCNMe2, migrates from the oxygen atom to the sulfur atom, forming an S-aryl thiocarbamate, ArSCNMe2...
.
Synthesis
Thiocarbamates can be synthesisedOrganic synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic molecules can often contain a higher level of complexity compared to purely inorganic compounds, so the synthesis of organic compounds has...
by hydrolysis
Hydrolysis
Hydrolysis is a chemical reaction during which molecules of water are split into hydrogen cations and hydroxide anions in the process of a chemical mechanism. It is the type of reaction that is used to break down certain polymers, especially those made by condensation polymerization...
of thiocyanates:
- RSCN + H2O → RSC(=O)NH2
Where R is aryl
Aryl
In the context of organic molecules, aryl refers to any functional group or substituent derived from an aromatic ring, be it phenyl, naphthyl, thienyl, indolyl, etc....
, this method is known as the Riemschneider thiocarbamate synthesis
Riemschneider thiocarbamate synthesis
The 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....
.