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Tricyclobutabenzene

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 often display unusual conformations and because of their unusual reactivity. Tricyclobutabenzenes are isomers of radialenes 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 250 C.

:[[File:Tricyclobutadiene synthesis.png|500px|Synthesis of tricyclobutabenzene]]

A polyoxygenated tricyclobutabenzene with an extraordinary bond length of 160 pm for the bond connecting two carbonyl groups by the following sequence:

:[[File:Tricyclobutabenzene polyoxygenated.png|500px|Polyoxygenated tricyclobutabenzene]]

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.

:[[File:Benzotriyne synthon.png|200px|Scheme 3 Benztriyne synthon]]

References

References

  1. ''Tricyclobutabenzene'' Wutichai Nutakul, Randolph P. Thummel, Austin D. Taggart [[J. Am. Chem. Soc.]]; '''1979'''; 101(3); 770-771. {{doi. 10.1021/ja00497a064
  2. Reaction sequence: [[coupling reaction]] of cyclobutene [[Grignard reaction. Grignard reagents]] followed by [[Diels–Alder reaction]] with dimethylcyclobutene-1,2-dicarboxylate, followed by [[ester]] [[hydrolysis]] to di[[carboxylic acid]] with [[potassium hydroxide]] in [[methanol]] followed by [[decarboxylation]] and [[aromatization]] with [[lead tetraacetate]]
  3. ''Poly-Oxygenated Tricyclobutabenzenes via Repeated [2 + 2] Cycloaddition of Benzyne and Ketene Silyl Acetal'' Toshiyuki Hamura, Yousuke Ibusuki, Hidehiro Uekusa, Takashi Matsumoto, and Keisuke Suzuki[[J. Am. Chem. Soc.]]; '''2006'''; 128(11) pp 3534 - 3535; {{doi. 10.1021/ja0602647
  4. Reaction sequence: the key step is a [2+2] [[cycloaddition]] between an [[aryne]] formed from the iodotriflate by action of [[N-Butyllithium. ''n''-butyllithium]] and a ketene silyl acetal. The silyl acetal is then converted to a [[ketone]] group by [[hydrofluoric acid]] and the remaining [[acetal]] groups by reaction with [[boron trifluoride]]
  5. ''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.]]; '''2006'''; 128(31) pp 10032 - 10033; {{doi. 10.1021/ja064063e
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polycyclic-aromatic-hydrocarbons tetracyclic-compounds cyclobutanes cyclobutenes
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