The mechanism of reduction of nitrosobenzene by alcohols

Abstract

Nitrosobenzene is easily reduced to azoxybenzene by alkaline aqueous solutions of alcohols. Combined kinetic and product studies indicate that this reduction involves a hydride transfer, probably from an alkoxide anion, to give the anion of phenylhydroxylamine which then combines rapidly with a second molecule of nitrosobenzene to form azoxybenzene. Only the latter reaction involves the formation of nitrosobenzene anion-radicals, (PhNO·)^–. The one-electron reduction of nitrosobenzene could not be effected by hydrocarbons such as cumene or by sym-trisubstituted phenols.