The mechanism of reduction of nitrosobenzene by alcohols

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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.

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