Oxidative cyclizations. II. Kinetic studies of the reaction of 2-nitroaniline with phenyliodoso acetate in toluene solution

Abstract

A kinetic study of the oxidation of 2-nitroaniline by phenyliodoso acetate in toluene solution reveals that the reaction is first order in both amine and oxidant. The mass action effects of products on oxidation rate demonstrate that at least two stages are involved in the reaction, and that the mass action effect of acetic acid is exerted only by its monomer. Evidence is obtained for the formation of an intermediate containing trivalent iodine. All these facts are consistent with the mechanism previously proposed by us for this reaction.