Tetrahedron

Study of the mechanism of base induced dehydrobromination of trans-β-bromostyrene

M Mąkosza, AA Chesnokov

Index: Makosza, Mieczyslaw; Chesnokov, Alexey A. Tetrahedron, 2003 , vol. 59, # 11 p. 1995 - 2000

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Citation Number: 11

Abstract

Observation that rates of dehydrobromination of trans-β-bromostyrene (1) and the Hofmann degradation of tetrabutyl ammonium cation depend on strength of base in different ways and that treatment of 1 with base results in fast abstraction of the β-proton imply the possibility that the dehydrobromination of 1 could proceed via α-elimination and Ph migration. In order to clarify this question, β-13C-labeled 1 was obtained and subjected to PTC ...

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