Helvetica Chimica Acta

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

KB Becker

Index: Becker,K.B. Helvetica Chimica Acta, 1977 , vol. 60, p. 81 - 93

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Citation Number: 25

Abstract

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., ...