Tricyclobutabenzene Polyoxygenated on:
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Tricyclobutabenzene is an 
A polyoxygenated tricyclobutabenzene with an extraordinary 
An ordinary bond of this type is only 148 pm and for comparison the C-C bond in 
aromatic hydrocarbon
Aromatic compounds, also known as "mono- and polycyclic aromatic hydrocarbons", are organic compounds containing one or more aromatic rings. The parent member of aromatic compounds is benzene. The word "aromatic" originates from the past grou ...
consisting of a benzene
Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen ato ...
core with three cyclobutane
Cyclobutane is a cycloalkane and organic compound with the formula (CH2)4. Cyclobutane is a colourless gas and commercially available as a liquefied gas. Derivatives of cyclobutane are called cyclobutanes. Cyclobutane itself is of no commercia ...
rings fused onto it. This compound and related compounds are studied in the laboratory because they are often displaying unusual conformations and because of their unusual reactivity. Tricyclobutabenzenes are isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers.
...
s of radialene are alicyclic organic compounds containing n cross-conjugated exocyclic double bonds. The double bonds are commonly alkene groups but those with a carbonyl (C=O) group are also called radialenes. For some members the unsubstituted parent radialen ...
s and form an equilibrium with them.
The parent tricyclobutabenzene (C12H12) was first synthesised in 1979 by the following sequence: This compound is stable up to .
:
A polyoxygenated tricyclobutabenzene with an extraordinary bond length
In molecular geometry, bond length or bond distance is defined as the average distance between nuclei of two bonded atoms in a molecule. It is a transferable property of a bond between atoms of fixed types, relatively independent of the rest ...
of 160 pm for the bond connecting two carbonyl groups by the following sequence:
:
An ordinary bond of this type is only 148 pm and for comparison the C-C bond in isatin
Isatin, also known as tribulin, is an organic compound derived from indole with formula C8H5NO2. The compound was first obtained by Otto Linné Erdman and Auguste Laurent in 1840 as a product from the oxidation of indigo dye by nitric acid and ...
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
In chemistry, an oxocarbon or oxide of carbon is a chemical compound consisting only of carbon and oxygen. The simplest and most common oxocarbons are carbon monoxide (CO) and carbon dioxide (). Many other stable (practically if not thermodynamica ...
.''Dodecamethoxy- and Hexaoxotricyclobutabenzene: Synthesis and Characterization'' Toshiyuki Hamura, Yousuke Ibusuki, Hidehiro Uekusa, Takashi Matsumoto, Jay S. Siegel, Kim K. Baldridge, and Keisuke Suzuki J. Am. Chem. Soc.
The ''Journal of the American Chemical Society'' is a weekly peer-reviewed scientific journal that was established in 1879 by the American Chemical Society. The journal has absorbed two other publications in its history, the ''Journal of Analytical ...
; 2006; 128(31) pp 10032 - 10033; A key starting material is the iodo triflate depicted below which is a benzotriyne synthon
In retrosynthetic analysis, a synthon is a hypothetical unit within a target molecule that represents a potential starting reagent in the retroactive synthesis of that target molecule. The term was coined in 1967 by E. J. Corey. He noted in 198 ...
.
:
See also
* Biphenyl *Triphenyl
Terphenyls are a group of closely related aromatic hydrocarbons. Also known as diphenylbenzenes or triphenyls, they consist of a central benzene ring substituted with two phenyl groups. There are three substitution patterns: ''ortho''-terphenyl ...
* Terpyridine
Terpyridine (2,2';6',2"-terpyridine, often abbreviated to Terpy or Tpy) is a heterocyclic compound derived from pyridine. It is a white solid that is soluble in most organic solvents. The compound is mainly used as a ligand in coordination chemis ...
* Terthiophene
Terthiophene is the organic compound with the formula 4H3Ssub>2C4H2S. It is an oligomer of the heterocycle thiophene, a shorter oligomer is dithienyl, and the parent polymer is polythiophene. In the most common isomer of terthiophene, two thie ...
* Naphthalene
Naphthalene is an organic compound with formula . It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromat ...
where the rings are fused
References
{{PAHs Polycyclic aromatic hydrocarbons Tetracyclic compounds Cyclobutanes Cyclobutenes