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Synthesis of 1-Bicyclo [3.2.2]nonene and 1 (7)-Bicyclo [3.2.2]nonene by Intramolecular Wittig Reaction

✍ Scribed by Konrad B. Becker; Jacques L. Chappuis

Publisher: John Wiley and Sons
Year: 1980
Tongue: German
Volume: 63
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19800630709

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✦ Synopsis

Abstract

The synthesis of 1‐bicyclo[3.2.2]nonene (2) and of 1 (7)‐bicyclo [3.2.2]nonene (3), two isomeric bridged (E)‐cycloheptenes, by intramolecular Wittig reaction is described. These ‘Bredt olefins’ could not be isolated, but dimerized rapidly. In both cases, the main product was shown to be a head‐to‐tail dimer with a cyclobutane ring. The ‘Bredt olefins’ were also trapped in situ with furan or 2,5‐diphenylbenzo [c]furan.

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## Abstract Starting from the easily accesible chiral aldehyde 2, we obtained enantiomerically pure (__Z__)‐ and (__E__)‐α,‐chloro‐α,β‐unsaturated esters 4c in good yields by olefination reactions. (__Z__)‐and (__E__)‐4c were allowed to react with the kinetically controlled generated lithium dienol