4-Bromocyclopentene by Hydride Reduction of 3, 5-Dibromocyclopentene and Its Unassisted Hydrolysis

PD Barlett, MR Rice

Index: Barlett,P.D.; Rice,M.R. Journal of Organic Chemistry, 1963 , vol. 28, p. 3351 - 3353

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Citation Number: 2

Abstract

A preparation of 4bromocyclopentene is described by the reaction of lithium aluminum hydride with the dibromide prepared from cyclopentadiene. This homoallylic bromide undergoes solvolysis in 50% aqueous acetone about four times less rapidly than cyclopentyl bromide. Its unreactivity is discussed in the light of the acceleration by 1011 observed in the related but strained 7-norbornenyl sulfonates.