Abstract
Tin(ii) chloride selectively reduces the aromatic nitro group to the amino group, the azoxy group remaining intact. This allows the preparation of 2-(R-NNO-azoxy)anilines from 2-(R-NNO-azoxy)nitrobenzenes bearing electron-donating or weak electron-withdrawing substituents (Me or Br) in the benzene ring and alkyl substituents at the distal N atom of the azoxy group. The presence of electron-withdrawing substituents at the azoxy group (for example, CO2Et) leads to a change in the direction of the reaction resulting in selective reduction of the azoxy group to the hydrazo group.
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Lipilin, D.L., Churakov, A.M., Strelenko, Y.A. et al. Selective reduction of the nitro group in the presence of the azoxy group. Synthesis of 2-(alkyl-NNO-azoxy)anilines. Russian Chemical Bulletin 51, 311–318 (2002). https://doi.org/10.1023/A:1015463912286
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DOI: https://doi.org/10.1023/A:1015463912286