Russian Chemical Bulletin

, Volume 58, Issue 10, pp 2047–2057 | Cite as

Synthesis and properties of N-nitro-O-(4-nitrophenyl)hydroxylamine

  • M. S. Klenov
  • A. M. Churakov
  • O. V. Anikin
  • Yu. A. Strelenko
  • V. A. Tartakovsky
Full Articles


Salts of N-nitro-O-(4-nitrophenyl)hydroxylamine were synthesized by a new method of oxidative nitration, involving the reaction of O-(4-nitrophenyl)hydroxylamine with KNO2 or NaNO2 in the presence of PhI(OAc)2 or PhIO as oxidants. When using Na15NO2, the samples containing the nitro group labeled with the 15N isotope were obtained. Acidification of the appropriate salt gave N-nitro-O-(4-nitrophenyl)hydroxylamine. It is the first N-nitrohydroxylamine isolated in the H-form. Its thermal stability was investigated and the probable mechanism of decomposition was suggested. From a comparison of the 14N and 15N NMR spectra of N-nitro-O-(4-nitrophenyl)hydroxylamine with those of its O- and N-methylated derivatives, its equilibrium with the aci-form (N=NOOH) was inferred.

Key words

hydroxylamines nitrohydroxylamines oxidative nitration oxodiazonium ion thermal stability 11314and 15N NMR spectra 


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Copyright information

© Springer Science+Business Media, Inc.  2009

Authors and Affiliations

  • M. S. Klenov
    • 1
  • A. M. Churakov
    • 1
  • O. V. Anikin
    • 1
  • Yu. A. Strelenko
    • 1
  • V. A. Tartakovsky
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussia Federation

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