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Tricyclobutabenzene

From Wikipedia, the free encyclopedia
Tricyclobutabenzene
Names
Preferred IUPAC name
Tetracyclo[8.2.0.02,5.06,9]dodeca-1,5,9-triene
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C12H12/c1-2-8-7(1)9-3-4-11(9)12-6-5-10(8)12/h1-6H2 checkY
    Key: MTPUNWSZJLTTLU-UHFFFAOYSA-N checkY
  • InChI=1/C12H12/c1-2-8-7(1)9-3-4-11(9)12-6-5-10(8)12/h1-6H2
    Key: MTPUNWSZJLTTLU-UHFFFAOYAI
  • c12c4c(c3c(c1CC2)CC3)CC4
Properties
C12H12
Molar mass156.228 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Tricyclobutabenzene is anaromatic hydrocarbon consisting of abenzene core with threecyclobutane rings fused onto it. This compound and related compounds are studied in the laboratory because they often display unusualconformations and because of their unusual reactivity. Tricyclobutabenzenes areisomers ofradialenes and form anequilibrium with them.

The parent tricyclobutabenzene (C12H12) was firstsynthesised in 1979[1] by the following sequence:[2][3] This compound is stable up to 250 °C (482 °F).

Synthesis of tricyclobutabenzene

A polyoxygenated tricyclobutabenzene with an extraordinarybond length of 160pm for the bond connecting two carbonyl groups[1] by the following sequence:[4]

Polyoxygenated tricyclobutabenzene

An ordinary bond of this type is only 148 pm and for comparison the C-C bond inisatin is 154 pm long. On the other hand, no change is recorded in the aromatic bond length alternation.

Similar chemistry yielded the six-fold ketonehexaoxotricyclobutabenzene C12O6, which happens to be a noveloxide of carbon.[5] A key starting material is the iodo triflate depicted below which is abenzotriynesynthon.

Scheme 3 Benztriyne synthon

See also

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References

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  1. ^Tricyclobutabenzene Wutichai Nutakul, Randolph P. Thummel, Austin D. TaggartJ. Am. Chem. Soc.;1979; 101(3); 770-771.doi:10.1021/ja00497a064
  2. ^Reaction sequence:coupling reaction of cyclobuteneGrignard reagents followed byDiels–Alder reaction with dimethylcyclobutene-1,2-dicarboxylate, followed byesterhydrolysis to dicarboxylic acid withpotassium hydroxide inmethanol followed bydecarboxylation andaromatization withlead 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 SuzukiJ. 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 anaryne formed from the iodotriflate by action ofn-butyllithium and a ketene silyl acetal. The silyl acetal is then converted to aketone group byhydrofluoric acid and the remainingacetal groups by reaction withboron trifluoride
  5. ^Dodecamethoxy- and Hexaoxotricyclobutabenzene: Synthesis and Characterization Toshiyuki Hamura, Yousuke Ibusuki, Hidehiro Uekusa, Takashi Matsumoto, Jay S. Siegel, Kim K. Baldridge, and Keisuke SuzukiJ. Am. Chem. Soc.;2006; 128(31) pp 10032 - 10033;doi:10.1021/ja064063e
2 rings
3 rings
4 rings
5 rings
6 rings
7+ rings
General classes
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