Chemoselective reduction of 1-nitro-2-(2-nitro-2-methylpropyl)-benzene to 2,2′-di-(2-nitro-2-methylpropyl)-azoxybenzene was achieved with sodium borohydride in methanol in the presence of substoichiometric amounts of bismuth, whereas reduction with zinc in hydrochloric acid gave a mixture of the latter, 1-amino-2-(2-amino-2-methylpropyl)-benzene, and 3,3-dimethyl-3,4-dihydrocinnoline, and showed poor reproducibility. The crystal structure of the azoxybenzene was determined by single-crystal X-ray diffraction.
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Received August 26, 2002; accepted September 2, 2002
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Siemeling, U., Türk, T., Vorfeld, U. et al. Selective Reduction of an Aromatic Nitro Group to an Azoxy Unit in the Presence of an Aliphatic Nitro Group. Monatshefte für Chemie 134, 419–423 (2003). https://doi.org/10.1007/s00706-002-0549-9