The Reduction of Some 2,2'-Dinitrodiaryl Compounds and Related Compounds by Thiourea S,S-Dioxide (Formamidinesulfinic Acid)

Abstract

The reaction of thiourea S,S-dioxide ( formamidinesulfinic acid) in ethanolic alkali with 2,2?-dinitrobiphenyl and several related dinitro compounds possessing an -X-bridge (where X = NH, NMe , O and S), located at the 1,1′-positions, has been investigated. With 2,2′-dinitrobiphenyl ′(which gives good yields of benzo [c] cinnoline and its oxides) and, to a minor extent, with 2,2′-dinitrodiphenylamine, anintramolecular reaction occurred to give heterocyclic products; with each of the other dinitro compounds, the only product obtained was formed as the result of a Smiles rearrangement.