Polyquinane

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A polyquinane and polyquinene is a saturated or unsaturated, respectively, polycyclic hydrocarbon consisting of fused five-membered rings [1]. The simplest member is the bicyclic compound bicyclo[3.3.0]octane. Other members are triquinacene and dodecahedrane.

[edit] Triquinacene

triquinacene

The compound triquinacene (tricyclo[5.2.1.-04,10]deca-2,5,8-triene) is the second member of a family of polyquinenes. It was synthesized in 1964 in the group of R. B. Woodward[2] in connection with its suspected homoaromatic properties (found to have none) and also as part of an attempt to synthesize the then elusive and much coveted compound dodecahedrane (the attempt failed). Unlike the related pentacene, this compound is stable with a melting point of 18°C. The final step in its synthesis is a variation of the Hofmann elimination (hydrogen peroxide converts the amine to the amine oxide then: pyrolysis).

triquinacene synthesis Woodward 1965

[edit] See also

  • Fused 6 membered rings: the acenes
  • triquinacene is Isomeric with: bullvalene, diisopropenyldiacetylene

[edit] References

  1. ^ Gold Book definition Link
  2. ^ R. B. Woodward, T. Fukunaga, R. C. Kelly J. Am. Chem. Soc. (86). "Triquinacene". Journal of the American Chemical Society 86 (15): 3162–3164. doi:10.1021/ja01069a046.