Preparation of hexacyclo[6.6.0.02,6.03,13.04,11.05,9]tetradecane-10,14-dione and derivatives

Tahsin J. Chow, Tung-Kung Wu

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Abstract

The highly symmetrical structure of heptacyclo- [6.6.0.02,6.03,13.04,11.05,9.010,14]tetradecane (1) has attracted wide interest since its discovery in 1961.2,3 The synthesis of 1 can be completed in one step by coupling two units of norbornadiene through the mediation of certain transition metals. This reaction has provided an efficient method for the synthesis of a highly compact molecule which otherwise would be difficult to prepare.4 The cage geometry of these molecules makes them attractive to both organic and theoretical chemists.5 For a particular example, selective cleavage of two C-C bonds would produce a polyquinane with a folded geometry (cisoid fused) which might be used for a more efficient synthesis of dodeca- hedrane (Scheme I).6 In this report we describe the preparation of hexaquinanedione 2 and its derivatives by cutting open the cage of 1.

Original languageEnglish
Pages (from-to)1102-1103
Number of pages2
JournalJournal of Organic Chemistry
Volume53
Issue number5
DOIs
StatePublished - 1 Mar 1988

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