Journal of Organic Chemistry p. 1215 - 1217 (1984)
Update date:2022-08-04
Topics:
Chung, T. F.
Wu, Y. M.
Cheng, C. H.
Ethylenediamine selectively reduces aromatic nitro compounds RC6H4NO2 (R = H, m-CH3, p-CH3, and m-Ph) at 150 deg C to symmetric azo compounds RC6H4N=NC6H4R in good yield but does not reduce their ortho-substituted analogues.The diamine does not react with o- or p-nitroanilines but reduces the meta isomer to 1,3-diaminobenzene and 3,3'-diaminoazobenzene.Its reaction with o- and p-halonitrobenzenes gives substitution products H2NCH2CH2NHC6H4NO2.Nitrosobenzene is reduced to aniline and azobenzene, while α-nitroso-β-naphthol is converted to 1,4-phenanthroline.Among a variety of other amines tested, only 1,3-propylenediamine reduces nitrobenzene to azobenzene.A mechanism for the reaction is proposed.
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