Gibbs reaction. Part 1. Reduction of benzoquinone N-chloroimines to benzoquinone imines

Abstract

The behaviour of benzoquinone N-chloroimines under neutral, acidic, and basic conditions has been studied. Although these compounds are stable under neutral conditions they are hydrolysed in acidic solution to the corresponding benzoquinone derivatives. In the presence of base and alcohols, they are reduced to benzoquinone imines. Kinetic investigation of the reaction suggested an ionic mechanism, in which cleavage of the C_∝–H bond of the alcohol is the rate-determining step.