Journal of the American Chemical Society

Neighboring Carbon and Hydrogen. XXIX. ρ-σ Analysis of Acetolysis of Substituted Neophyl Arylsulfonates

R Heck, S Winstein

Index: Heck; Winstein Journal of the American Chemical Society, 1957 , vol. 79, p. 3432,3437

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Citation Number: 49

Abstract

In acetolysis of neophyl p-bromobenzenesulfonate, ionization is exclusively anchimerically assisted, only neighboring phenyl participating. Rates of aryl-assisted ionization of a series of substituted neophyl p-bromobenzenesulfonates have been measured and correlated with the aid of the Hammett pu relation. Omitting the $-Me0 group, log k of acetolysis is approximately linear in u with a slope p of-3.65. The value of log k for the p-Me0 ...