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Preparation ofN-nitrohydroxylamines by direct nitration

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Abstract

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 thatN-methyl-O-2,4-dinitro- and 2,4,6-trinitrophenylhydroxylamines undergo nitration with nitronium tetrafluoroborate or with a mixture of nitric acid and acetic anhydride to give the correspondingN-nitrohydroxylamines in high yields.N-Nitro-2,4-dinitrohydroxylamine that contains no methyl group at the nitrogen atom is unstable and forms a product ofO-alkylation upon reaction with diazomethane.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation

    E. N. Khodot, I. M. Petrova, O. V. Anikin & I. E. Chlenov

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  1. E. N. Khodot
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  2. I. M. Petrova
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  3. O. V. Anikin
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  4. I. E. Chlenov
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Additional information

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2276–2278, November, 1995.

The work was supported by the International Science Foundation (Grant NGN 000).

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Khodot, E.N., Petrova, I.M., Anikin, O.V. et al. Preparation ofN-nitrohydroxylamines by direct nitration. Russ Chem Bull 44, 2183–2185 (1995). https://doi.org/10.1007/BF00696728

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  • DOI: https://doi.org/10.1007/BF00696728

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