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Russian Chemical Bulletin

, Volume 60, Issue 5, pp 855–860 | Cite as

A study of the reaction mechanism of 3-nitro-4-R-furoxans formation by nitrosation of dipotassium salts of 1-hydroxyimino-2,2-dinitro-1-R-ethanes

  • I. V. Ovchinnikov
  • Yu. A. Strelenko
  • N. A. Popov
  • A. O. Finogenov
  • N. N. Makhova
Full Articles

Abstract

The mechanism proposed earlier for explanation of the furoxan ring formation in the nitrosation of dipotassium salts of 1-hydroxyimino-2,2-dinitro-1-R-ethanes with NaNO2/AcOH was confirmed experimentally by determining the ionization constants of the dinitromethyl and oxime fragments in the starting dipotassium salt and by examining 1H, 13C, 14N, and 15N NMR and mass spectra of isomeric 3(4)-nitro-4(3)-R-furoxans with the 15N(5) and 15N(2) ring atoms, respectively, and 3,4-diarylfuroxan with both 15N-labeled ring atoms. A comparative analysis of the IR and Raman spectra of the 15N-labeled furoxan derivatives obtained and their unlabeled analogs allowed refinement of the literature data on interpretation of the vibrational spectra of furoxan derivatives.

Key words

mechanism nitrosation dipotassium salts of 1-hydroxyimino-2,2-dinitro-1-Rethanes ionization constants isomeric 15N-labeled 3(4)-nitro-4(3)-R-furoxans 15N-labeled 3,4-diarylfuroxan 11314and 15N NMR spectra IR spectroscopy mass spectrometry 13C-15N coupling constants 

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Copyright information

© Springer-Verlag 2011

Authors and Affiliations

  • I. V. Ovchinnikov
    • 1
  • Yu. A. Strelenko
    • 1
  • N. A. Popov
    • 1
  • A. O. Finogenov
    • 1
  • N. N. Makhova
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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