An investigation of the reaction of primary nitroalkanes with acetic anhydride/sodium acetate

Article abstract of DOI:10.1016/S0040-4020(01)97248-5

Oxidation of primary nitroalkanes by acetic anhydride/sodium acetate has been found to be more complex than previously suspected. Phenylnitromethane, with acetic anhydride/sodium acetate at 60-80°, for example, gives a mixture of benzoic anhydride, triacethylhydroxylamine and acetanilide, through the mixed anhydride {A figure is presented} as a key intermediate. Evidence in support of this latter species has been obtained by carrying out the oxidation in the presence of dimethyl acetylenedicarboxylate as a 1,3-dipolarophile, when 3-phenyl-4,5-dicarbomethoxyisoxazole is formed in 82% yield. A number of other 3-alkyl- and 3-aryl-4,5-dicarbomethoxyisoxazoles have been prepared in a similar manner.