Abstract
A series of ring substituted benzylchlorides have been reacted under photolytic conditions with bromotrichloromethane at 70°. Competitive kinetics show the bromination reaction to be substantially dependent upon ring substituents. A rho value of −1.02 (correlating with σ +) was obtained with a correlation coefficient of −0.996. This is greater than has been observed for other α-substituted toluenes and is attributed to the slight radical destabilizing effect of the adjacent chlorine atom. A correlation between the ring substituent effects in various series of α-substituted toluenes and the electronic and steric requirements of the α-substituent has been developed.
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