Chemistry of Heterocyclic Compounds

, Volume 21, Issue 9, pp 982–984 | Cite as

Dipolar addition of diazomethane to 5-methylene-1,3-dioxolan-4-one

  • V. R. Likhterov
  • V. S. Étlis
Article
  • 81 Downloads

Abstract

The reactions of 1-pyrazoline-3-spiro-4′-(1′,3′-dioxolan-5′-one) were studied; this compound is the product of the 1,3-dipolar addition of diazomethane to 5-methylene-1,3-dioxolan-4-one. Depending on the conditions, thermolysis of the spiro compounds proceeds either with destruction of the pyrazoline ring, or with cleavage of the dioxolane ring, followed by rearrangement to give 1(2)-hydroxymethyl-3(5)-pyrazolecarboxylic acid.

Keywords

Organic Chemistry Thermolysis Spiro Diazomethane Pyrazoline 

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Literature cited

  1. 1.
    Yu. A. Kotikyan, P. V. Petrovskii, B. A. Dyatkin, and I. L. Knunyants, Zh. Org. Khim., 7, 1363 (1971).Google Scholar
  2. 2.
    V. R. Likhterov, Khim. Geterosikl. Soedin., No. 4, 545 (1973).Google Scholar
  3. 3.
    V. R. Likhterov, V. S. Étlis, L. A. Baladina, and S. A. Arzhanov, A. p. 606313 (USSR); Byull. Izobr., No. 6, 215 (1984).Google Scholar
  4. 4.
    Heterocyclic Compounds, R. Elderfield, eds., Vol. 5, Wiley (1957).Google Scholar
  5. 5.
    B. V. Ioffe, Khim. Geterosikl. Soedin., No. 6, 1089 (1968).Google Scholar
  6. 6.
    M. Farines and J. Soulier, Bull. Soc. Chim. Fr., No. 1, 332 (1970).Google Scholar
  7. 7.
    J. F. Walker, Formaldehyde, Reinhold (1964).Google Scholar
  8. 8.
    R. Hüttel and P. Jochem, Chem. Ber., 85, 820 (1952).Google Scholar
  9. 9.
    D. C. Ayres, Carbanions in Synthesis [Russian translation], Khimiya, Leningrad (1969), p. 199.Google Scholar
  10. 10.
    Comprehensive Organic Chemistry [Russian translation], D. Barton and W. D. Ollis, eds., Vol. 3, Khimiya, Moscow (1982), p. 306.Google Scholar
  11. 11.
    H.-G. Heine and D. Wendisch, Ann. Chem., 3, 463 (1976).Google Scholar
  12. 12.
    F. Arndt, Synthesis of Organic Compounds [Russian translation], Moscow, Foreign Literature Press, 2, 174 (1949).Google Scholar

Copyright information

© Plenum Publishing Corporation 1986

Authors and Affiliations

  • V. R. Likhterov
  • V. S. Étlis

There are no affiliations available

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