Polyquinane

A polyquinane and polyquinene is a saturated or unsaturated, respectively, polycyclic hydrocarbon consisting of fused five-membered rings [Gold Book definition [http://goldbook.iupac.org/P04751-plain.html Link] ] . The simplest member is the bicyclic compound bicyclo [3.3.0] octane. Other members are triquinacene and dodecahedrane.

Triquinacene

[cite journal
title = Triquinacene
author = R. B. Woodward, T. Fukunaga, R. C. Kelly J. Am. Chem. Soc.
year = 86
issue =15
pages = 3162–3164
doi = 10.1021/ja01069a046
journal = Journal of the American Chemical Society
volume = 86] 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).

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See also

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

References