My watch list  


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.


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).

See also

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


  1. ^ Gold Book definition Link
  2. ^ R. B. Woodward, T. Fukunaga, R. C. Kelly J. Am. Chem. Soc. (86). "Triquinacene" (15): 3162 - 3164. doi:10.1021/ja01069a046.
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Polyquinane". A list of authors is available in Wikipedia.
Your browser is not current. Microsoft Internet Explorer 6.0 does not support some functions on Chemie.DE