Preparation of N-nitrohydroxyamines by diresct nitration

Article abstract of DOI:10.1007/BF00696728

The possibilities for stabilization of compounds with the A-B-NO2 fragment, where A is an atom containing a lone electron pair, were examined.It was shown that N-methyl-O-2,4-dinitro- and 2,4,6-trinitrophenylhydroxyamines undergo nitration with nitronium tetrafluoroborate or with a mixture of nitric acid and acetic anhydride to give the corresponding N-nitrohydroxylamines in high yields.N-Nitro-2,4-dinitrohydroxylamine that contains no methyl group at the nitrogen atom is unstable and forms a product of O-alkylation upon reaction with diazomethane. - Key words: N-nitrohydroxylamines; nitration.