Chemistry of Heterocyclic Compounds

, Volume 22, Issue 2, pp 161–166 | Cite as

Reactions of azirines with sulfur nucleophiles. 4. Treatment of 2H-azirine with mercaptosubstituted acids. reactions of aziridinyl alkyl sulfides with carboxylic acids and acyl chloride derivatives

  • R. S. Él'kinson
  • A. V. Eremeev


Treatment of 2H-azirines with mercaptosubstituted acids and their derivatives leads to β-ketoamides and 2-aziridinyl alkyl sulfides, respectively. 2-Aziridinyl alkyl sulfides, in turn, react with carboxylic acids to give β-ketoamides and substituted ethanethiol derivatives. Acylation of 2-aziridinyl alkyl sulfides with acyl halides generates a variety of products, depending on the reaction conditions; either products derived from cleavage and isomerization of the aziridinyl ring or (1-acylaziridinyl-2) alkyl sulfides are obtained.


Sulfur Chloride Sulfide Organic Chemistry Carboxylic Acid 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    R. S. Él'kinson, A. V. Eremeev, Ya. Ya. Bleidelis, A. F. Mishnev, and S. V. Belyakov, Khim. Geterotsikl. Soedin., No. 12, 1633 (1985).Google Scholar
  2. 2.
    A. V. Eremeev and R. S. Él'kinson, Khim. Geterotsikl. Soedin., No. 6, 736 (1984).Google Scholar
  3. 3.
    R. S. Él'kinson, A. V. Eremeev, A. F. Mishnev, Ya. Ya. Bleidelis, and V. G. Semenikhina, Khim. Geterotsikl. Soedin., No. 1, 53 (1985).Google Scholar
  4. 4.
    J. Yukawa and S. Kimura, Patent No. 4,973 (Japan); Chem. Abst., 58, 1032 (1963).Google Scholar
  5. 5.
    R. F. Parcell, Chem. Ind., 33, 1396 (1963).Google Scholar
  6. 6.
    O. C. Dermer and G. E. Ham, Ethyleneimine and Other Aziridines, Academic Press, New York (1969).Google Scholar
  7. 7.
    H. C. Brown and A. Tsukamoto, J. Am. Chem. Soc., 83, 2016 (1961).Google Scholar
  8. 8.
    H. W. Heine, M. E. Fetter, and E. M. Nicholson, J. Am. Chem. Soc., 81, 2202 (1959).Google Scholar
  9. 9.
    H. Bestian, Ann., 566, 210 (1950).Google Scholar
  10. 10.
    R. S. Él'kinson, A. V. Eremeev, and É. É. Liepin'sh, Khim. Geterotsikl. Soedin., No. 5, 623 (1985).Google Scholar
  11. 11.
    A. Hassner, S. S. Burke, and I. Cheng-fan, J. Am. Chem. Soc., 97, 4692 (1975).Google Scholar

Copyright information

© Plenum Publishing Corporation 1986

Authors and Affiliations

  • R. S. Él'kinson
    • 1
  • A. V. Eremeev
    • 1
  1. 1.Institute of Organic SynthesisAcademy of Sciences of the Latvian SSRRiga

Personalised recommendations