NITRATION AND REDUCTION OF SUBSTITUTED AZOBENZENES AND AZOXYBENZENES

The nitration of some symmetrically tetrasubstituted azo- and azoxy-benzenes in various nitrating media was found to yield the 4-nitro derivatives in some cases, while more drastic conditions gave the 4,4′-dinitro compounds. Some nitroazobenzenes were transformed to the 4-nitroazo and 4,4′-dinitroazoxy derivatives.Reduction of the mononitroazo-, dinitroazo-, and azoxy-benzenes gave the monoaminoazo, diaminoazo, and azoxy derivatives under mild conditions while strong reducing agents converted the whole molecule to 1,4-diaminobenzene. One exception was found with 2,2′,5,5′-tetramethyl-4,4′-dinitroazobenzene, which was reduced to 2,2′,5,5′-tetramethyl-4,4′-dinitrohydrazobenzene.