Chemistry of Heterocyclic Compounds

, Volume 10, Issue 3, pp 290–295 | Cite as

Some peculiarities of the cyclization of N-polynitroalkyl-N-nitrosoaminoacetic acids and their nitriles to sydnones and sydnonimines

  • A. L. Fridman
  • F. M. Mukhametshin
  • V. S. Zalesov
  • S. S. Novikov


The cyclization of N-polynitroalkyl-N-nitrosoaminoacetic acids to sydnones occurs only under the influence of trifluoroacetic anhydride. Closing to a sydnonimine ring does not occur in the case of N-(2,2,2-trinitroethyl)-N-nitrosoaminoacetonitrile, but N-(2,2,2-trinitroethyl)-N-nitrosoiminoacetic acid imino ester is formed. Removal of the nitro groups in the γ position relative to the nitrosoamino group leads to normal occurrence of the reaction to give polynitroalkylsydnonimines.


Ester Organic Chemistry Nitrile Anhydride Nitro Group 
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Literature cited

  1. 1.
    F. M. Mukhametshin, A. L. Fridman, and A. D. Nikolaeva, Khim. Geterotsikl. Soedin., 125 (1970).Google Scholar
  2. 2.
    W. Baker and W. Ollis, Quart. Rev., 2, 15 (1957).Google Scholar
  3. 3.
    F. Stewart, Chem. Rev., 64, 129 (1964).Google Scholar
  4. 4.
    A. L. Fridman, F. M. Mukhametshin, and S. S. Novikov, Usp. Khim., 40, 65 (1971).Google Scholar
  5. 5.
    R. Williams, R. Pace, and G. Jeacocke, Spectrochim. Acta, 20, 225 (1964).Google Scholar
  6. 6.
    F. M. Mukhametshin and A. L. Fridman, Zh. Organ. Khim., 6, 928 (1970).Google Scholar
  7. 7.
    A. L. Fridman, V. P. Ivshin, and S. S. Novikov, Usp. Khim., 38, 1448 (1969).Google Scholar
  8. 8.
    V. I. Slovetskii, Usp. Khim., 40, 740 (1971).Google Scholar
  9. 9.
    N. Marans and R. Zelinsky, J. Am. Chem. Soc., 72, 5329 (1950).Google Scholar
  10. 10.
    H. Feuer, G. Bachman, C. Coller, and W. Swarts, Tetrahedron, 19 (lI), 165 (1963).Google Scholar
  11. 11.
    H. Ungnade and L. Kissinger, Tetrahedron, 19 (I), 143 (1963).Google Scholar
  12. 12.
    J. Bailey and D. Shyder, J. Am. Chem. Soc., 37, 935 (1915).Google Scholar
  13. 13.
    L. Herzog, M. Gold, and E. Geckler, J. Am. Chem. Soc., 73, 749 (1951).Google Scholar
  14. 14.
    G. Gold, M. Frankel, G. Linden, and K. Klager, J. Org. Chem., 27, 334 (1962).Google Scholar

Copyright information

© Plenum Publishing Corporation 1975

Authors and Affiliations

  • A. L. Fridman
    • 1
  • F. M. Mukhametshin
    • 1
  • V. S. Zalesov
    • 1
  • S. S. Novikov
    • 1
  1. 1.Perm State Pharmaceutical Institute. N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow

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