Polar Effects in the Homoallylic Rearrangement of Arylcyclopropylcarbinols

S Sarel, E Breuer, S Ertag…

Index: Sarel,S. et al. Israel Journal of Chemistry, 1963 , vol. 1, p. 451 - 459

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Citation Number: 8

Abstract

Abstract The synthesis of some p-substituted phenylmethylcyclopropylcarbinols of the structure (I) is herein reported. Dehydration of the cyclopropylcarbinols by means of acetic anhydride yielded mixtures of α-cyclopropylstyrenes (V) and 4-arylpent-3-enyl acetates (VI) the ratio of which depended on both the polar characteristics of the substituent X and on reaction conditions. The relative order of the effect of substitution in the phenyl group on V/ ...