Oxidations with Iodosobenzene Diacetate. IX. A Kinetic investigation of the reaction with substituted-2-Nitroanilines

Abstract

Benzofurazan oxides are formed in excellent yield when certain substituted-2-nitroanilines react with iodosobenzene diacetate in benzene containing 1 per cent. (by volume) of acetic acid. The kinetics of this reaction have been studied. It is considered that the mechanism of the reaction involves a reversible reaction of the 2-nitroaniline with iodosobenzene diacetate to form acetic acid and an intermediate which is then converted to benzofurazan oxide, iodobenzene, and acetic acid. This reaction is therefore similar to the reaction of iodosobenzene diacetate with glycols. The rates of oxidation of substituted-2-nitroanilines could not be correlated with the electrical effect of the substituent. The reasons for this are discussed in detail.