Oxidative cyclizations. IV. Isokinetic relationship in the oxidation of orthosubstituted anilines with (diacetoxyiodo)benzene

Abstract

The rates of oxidative cyclization of 11 ortho-substituted anilines by (diacetoxyiodo)benzene have been measured in toluene-acetic acid solution. The activation parameters give a precise fit to an isokinetic relationship, which indicates that a common reaction mechanism is followed. This mechanism applies to amines from the benzene, naphthalene, and anthraquinone families, with nitro and various carbonyl and arylazo groups as the ortho substituents.