The Journal of Organic Chemistry

Reduction of aromatic nitro compounds by ethylenediamine. A new selective reagent for the synthesis of symmetric azo compounds

TF Chung, YM Wu, CH Cheng

Index: Chung, T. F.; Wu, Y. M.; Cheng, C. H. Journal of Organic Chemistry, 1984 , vol. 49, # 7 p. 1215 - 1217

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Citation Number: 16

Abstract

Ethylenediamine selectively reduces aromatic nitro compounds RC6H4NO2 (R= H, m-CH3, p-CH3, and m-Ph) at 150" C to symmetric azo compounds RC6H4N= NCa4R in good yield but does not reduce their ortho-substituted analogues. The diamine does not react with 0-or p-nitroanilines but reduces the meta isomer to 1, 3-diaminobenzene and 3, 3'- diaminoazobenzene. Its reaction with 0-and p-halonitrobenzenes gives substitution ...

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