Journal of the American Chemical Society

Preliminary studies of the mechanism of metal-halogen exchange. The kinetics of reaction of n-butyllithium with substituted bromobenzenes in hexane solution

HR Rogers, J Houk

Index: Rogers, Harold R.; Houk, Janette Journal of the American Chemical Society, 1982 , vol. 104, # 2 p. 522 - 525

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Citation Number: 42

Abstract

Abstract: Initial measurements of the rate of reaction of bromobenzene with n-butyllithium in hexane solution have shown the exchange to be first order in bromobenzene and first order in n-butyllithium, with an activation energy of 12 kcal mol-'(52 kJ mol-I). A Hammett relationship for the reaction of substituted bromobenzenes with n-butyllithium suggests negative charge character in the transition state (p= 2). The addition of a Lewis donor (p- ...