Reduction of nitrobenzene with sodium and lithium naphthalenide

Reduction of nitrobenzene with sodium or lithium naphthalenide results in formation of azobenzene and azoxybenzene in modest yields. With sodium naphthalenide, azoxybenzene formation is favored; use of lithium naphthalenide results in enhanced azobenzene yields. Reduction of azoxybenzene with naphthalenide results in azobenzene and a variety of fragmentation products. Hydrazobenzene was the only product formed upon azobenzene formation.