Polyquinane
title: "Polyquinane" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["polycyclic-nonaromatic-hydrocarbons", "cyclopentanes"] topic_path: "general/polycyclic-nonaromatic-hydrocarbons" source: "https://en.wikipedia.org/wiki/Polyquinane" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0
::figure[src="https://upload.wikimedia.org/wikipedia/commons/3/3d/Bicyclo(3.3.0)octane.png" caption="Bicyclo[3.3.0]octane"] ::
A polyquinane polycyclic compound consisting of fused five-membered hydrocarbon rings. If the compound is unsaturated instead of saturated, it is called a polyquinene. The simplest polyquinane is the bicyclic compound bicyclo[3.3.0]octane. Other members are triquinacene and dodecahedrane.
Triquinacene
::figure[src="https://upload.wikimedia.org/wikipedia/commons/3/35/Triquinacene_2.png" caption="Perspective image of triquinacene, a tricyclic polyquinene, has a cup-shaped geometry, suggesting a synthetic approach to dodecahedrane and possible interactions among its alkene regions"] ::
The compound triquinacene, sometimes simply called quinacene (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{{cite journal | title = Triquinacene | first1 = R. B. | last1 = Woodward | author1-link = Robert Burns Woodward | first2 = T. | last2 = Fukunaga | first3 = Robert C. | last3 = Kelly | year = 1964 | 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—though it was found to have no such properties—and also as part of a failed attempt to synthesize the then-elusive compound dodecahedrane. Triquinacene is stable, and has a melting point of 18 °C. The final step of its synthesis is a double Cope reaction to form two of the three alkenes.
:[[Image:TriquinaceneSynthesis.png|400px|triquinacene synthesis Woodward 1965]]
References
References
- "polyquinanes (polyquinenes)".
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