Y. Kusuyama, Takako Kubo, M. Iyo
Oct 1, 1991
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Influential Citations
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Journal
Bulletin of the Chemical Society of Japan
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 the benzene ring. The relative rates of the trans isomers at 45°C were best correlated by means of σm values with a ρ value of −3.14 and a correlation coefficient of 0.97, indicating that the cyclopropane ring was a poor transmitter of a resonance effect. The substituent effects were analyzed by means of the LSFE equation.