NITRATION AND REDUCTION OF SUBSTITUTED AZOBENZENES AND AZOXYBENZENES

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′-dinitroaz...

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Veröffentlicht in:Canadian journal of chemistry 1962-10, Vol.40 (10), p.1921-1925
Hauptverfasser: Singh, Joginder, Singh, Pritam, Boivin, Jean L, Gagnon, Paul E
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container_end_page 1925
container_issue 10
container_start_page 1921
container_title Canadian journal of chemistry
container_volume 40
creator Singh, Joginder
Singh, Pritam
Boivin, Jean L
Gagnon, Paul E
description 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.
doi_str_mv 10.1139/v62-295
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