Tricyclobutabenzene
Encyclopedia
Tricyclobutabenzene is an aromatic hydrocarbon
consisting of a benzene
core with three cyclobutane
rings fused onto it. This compound and related compounds are studied in the laboratory because they are often display unusual conformations and because of their unusual reactivity. Tricyclobutabenzenes are isomer
s of radialene
s with which they are able to interconvert.
The parent tricyclobutabenzene (C12H12) was first synthesized
in 1979 via a procedure depicted in Scheme 1. This compound is stable up to 250°C.
A polyoxygenated tricyclobutabenzene with an extraordinary bond length
of 160 pm for the bond connecting two carbonyl groups was synthesized according to scheme 2.
An ordinary bond of this type is only 148 pm and for comparison the C-C bond in isatin
is 154 pm long. On the other hand, no change is recorded in the aromatic bond length alternation.
Similar chemistry yielded the six-fold ketone hexaoxotricyclobutabenzene
C12O6, which happens to be a novel oxide of carbon
. A key starting material is the iodo triflate depicted below which is a benzotriyne
synthon
.
Hydrocarbon
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons from which one hydrogen atom has been removed are functional groups, called hydrocarbyls....
consisting of a benzene
Benzene
Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....
core with three cyclobutane
Cyclobutane
Cyclobutane is an organic compound with the formula 4. Cyclobutane is a colourless gas and commercially available as a liquefied gas. Derivatives of cyclobutane are called cyclobutanes...
rings fused onto it. This compound and related compounds are studied in the laboratory because they are often display unusual conformations and because of their unusual reactivity. Tricyclobutabenzenes are isomer
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...
s of radialene
Radialene
[n]Radialenes are alicyclic organic compounds containing n cross-conjugated exocyclic double bonds. The double bonds are commonly alkene groups but those with a carbonyl group are also called radialenes...
s with which they are able to interconvert.
The parent tricyclobutabenzene (C12H12) was first synthesized
Organic 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...
in 1979 via a procedure depicted in Scheme 1. This compound is stable up to 250°C.
A polyoxygenated tricyclobutabenzene with an extraordinary bond length
Bond length
- Explanation :Bond length is related to bond order, when more electrons participate in bond formation the bond will get shorter. Bond length is also inversely related to bond strength and the bond dissociation energy, as a stronger bond will be shorter...
of 160 pm for the bond connecting two carbonyl groups was synthesized according to scheme 2.
An ordinary bond of this type is only 148 pm and for comparison the C-C bond in isatin
Isatin
Isatin or 1H-indole-2,3-dione is an indole derivative. The compound was first obtained by Erdman and Laurent in 1841 as a product from the oxidation of indigo dye by nitric acid and chromic acids...
is 154 pm long. On the other hand, no change is recorded in the aromatic bond length alternation.
Similar chemistry yielded the six-fold ketone hexaoxotricyclobutabenzene
Hexaoxotricyclobutabenzene
Hexaoxotricyclobutabenzene is an organic compound with formula C12O6. It can be viewed as the sixfold ketone of tricyclobutabenzene. It is one of the novel oxides of carbon, detected by 13C NMR by T. Hamura and others in 2006....
C12O6, which happens to be a novel oxide of carbon
Oxocarbon
An oxocarbon or oxide of carbon is an inorganic compound consisting only of carbon and oxygen.The simplest and most common oxocarbons are carbon monoxide and carbon dioxide...
. A key starting material is the iodo triflate depicted below which is a benzotriyne
Benzotriyne
Benzotriyne or cyclo[6]carbon is a hypothetical chemical compound, an allotrope of carbon with molecular formula C6. The molecule is a ring of six carbon atoms, connected either by alternating triple and single bonds or by double bonds. It is, therefore, a potential member of the cyclo[n]carbon...
synthon
Synthon
A synthon is a concept in retrosynthetic analysis. It is defined as a structural unit within a molecule which is related to a possible synthetic operation. The term was coined by E.J. Corey...
.
See also
- BiphenylBiphenylBiphenyl is an organic compound that forms colorless crystals. It has a distinctively pleasant smell. Biphenyl is an aromatic hydrocarbon with a molecular formula 2...
- Triphenyl
- TerpyridineTerpyridineTerpyridine is a heterocyclic compound derived from pyridine. This colourless solid is used as a ligand in coordination chemistry.-Synthesis:...
- TerthiopheneTerthiopheneTerthiophene is the organic compound with the formula [C4H3S]2C4H2S. It is an oligomer of the heterocycle thiophene, a shorter oligomer is dithienyl, and the parent polymer is polythiophene...
- NaphthaleneNaphthaleneNaphthalene is an organic compound with formula . It is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromatic hydrocarbon, naphthalene's structure consists of a fused pair of benzene rings...
where the rings are fused