Substituent effects in the solvolysis of p-(2-substituted cyclopropyl)-α-methylbenzyl chlorides

Y Kusuyama, T Kubo, M Iyo, T Kagosaku…

Index: Kusuyama, Yoshiaki; Kubo, Takako; Iyo, Masami; Kagosaku, Tamami; Tokami, Kenjiro Bulletin of the Chemical Society of Japan, 1991 , vol. 64, # 10 p. 2954 - 2960

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Abstract

The solvolysis rates of p-(cis-or trans-2-substituted cyclopropyl)-α-methylbenzyl chlorides including electron-donating and electron-attracting substituents relative to a hydrogen substituent were measured in 80% aqueous acetone. The trans isomers were more reactive than the corresponding cis derivatives where cyclopropyl and phenyl groups could not get a most favorable “bisected” conformation for the cyclopropyl group to release electrons to ...