Abstract
The NaBH4 reduction of nitrosobenzene to hydrazobenzene/aniline≈3 : 1, phenylhydroxylamine to aniline, azoxybenzene to hydrazobenzene, azobenzene to hydrazobenzene, and hydrazobenzene to aniline is catalysed by bis(dimethylglyoximato)cobalt compounds (“cobaloximes”), CoCl2, and some other salts of transition metals. The NaBH4−CoCl2 system is a convenient and mild reducing agent which effects the reduction of e.g.trans-azobenzene to hydrazobenzene even at −60°C. The diazene configuration has no effect on the reduction of the N=N group;cis-fixed benzo[c]cinnoline is smoothly converted into 2.2′-diaminobiphenyl. Aliphatic diazeneslike 2.3-diazanorbornene andtrans-di-1-adamantyldiazene do not react.
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Avar, G., Kisch, H. Zur katalytischen Reduktion aromatischer Stickstoffverbindungen und Diazene in Gegenwart von Übergangsmetallverbindungen. Monatshefte für Chemie 109, 89–97 (1978). https://doi.org/10.1007/BF00911948
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DOI: https://doi.org/10.1007/BF00911948