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The Synthesis of Strained Methylene-bridged Bicyclic Olefins by the Intramolecular Wittig Reaction

✍ Scribed by Konrad B. Becker

Publisher
John Wiley and Sons
Year
1977
Tongue
German
Weight
800 KB
Volume
60
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

A convenient synthesis of the strained methylene‐bridged trans‐cyclooctenes bicyclo[3.3.1]‐1 (2)‐nonene (1), bicyclo[4.2.1]‐1(8)‐nonene (2), and bicyclo[4.2.1]‐1(2)‐nonene (3) by the intramolecular Wittig reaction is described (see Schemes 1–4). The (3‐oxocycloalkyl)alkyl‐phosphonium bromides 20, 27 and 38 undergoing cyclization to the bridgehead olefins are formed by simple reaction sequences. The spectral properties (IR., ^1^H‐NMR., ^13^C‐NMR., and UV.) of the olefins are discussed with regard to their strain.

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