Chemistry of Heterocyclic Compounds

, Volume 24, Issue 3, pp 264–267 | Cite as

Stereoselective trans-N-chlorination of the potassium salt of aziridine-2,2-dicarboxylic acid methyl ester

  • A. S. Moskalenko
  • I. I. Chervin
  • A. V. Prosyanik
  • R. G. Kostyanovskii
Article
  • 40 Downloads

Abstract

Primarily trans-1-chloroaziridine is formed in the chlorination of the potassium salt of aziridine-2,2-dicarboxylic acid methyl ester. The silver salt and then the mixed methyl ethyl ester, as well as the trimethylammonium and α-phenylethylammonium salts, were obtained from trans-1-chloroaziridine. Signals of diastereomers are observed in the PMR spectrum of the E isomer of the α-phenylethylammonium salt; this opens up the fundamental possibility of separation into antipodes.

Keywords

Methyl Ester Potassium Ethyl Organic Chemistry 

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Literature Cited

  1. 1.
    S. V. Varlamov, G. K. Kadorkina, and R. G. Kostyanovskii, Khim. Geterotsikl. Soedin., No. 3, 390 (1988).Google Scholar
  2. 2.
    R. G. Kostyanovskii, V. F. Rudchenko, A. V. Prosyanik, M. D. Isobaev, I. I. Chervin, and V. I. Markov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 3, 628 (1977).Google Scholar
  3. 3.
    A. B. Zolotoi, O. A. D'yachenko, L. O. Atovmyan, V. F. Rudchenko, I. I. Chervin, and R. G. Kostyanovskii, Khim. Geterotsikl. Soedin., No. 1, 48 (1984).Google Scholar
  4. 4.
    R. G. Kostyanovskii and V. F. Rudchenko, Dokl. Akad. Nauk SSSR, 231, 878 (1976).Google Scholar
  5. 5.
    A. V. Prosyanik, S. V. Bondarenko, and V. I. Markov, Zh. Org. Khim., 16, 1554 (1980).Google Scholar
  6. 6.
    P. G. Gassman and D. K. Dydon, J. Am. Chem. Soc., 91, 1543 (1969).Google Scholar
  7. 7.
    A. V. Prosyanik and A. S. Moskalenko, Zh. Org. Khim., 21, 2466 (1985).Google Scholar
  8. 8.
    R. G. Kostyanovskii, I. I. Chervin, V. A. Afanas'ev, A. A. Fomichev, and Z. E. Samoilova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 3, 726 (1969).Google Scholar
  9. 9.
    A. Forni, I. Moretti, G. Torre, S. Bruckner, L. Malpezzi, and G. DiSilvestro, J. Chem. Soc., Perkin Trans. 2, No. 4, 791 (1984).Google Scholar

Copyright information

© Plenum Publishing Corporation 1988

Authors and Affiliations

  • A. S. Moskalenko
    • 1
  • I. I. Chervin
    • 1
  • A. V. Prosyanik
    • 1
  • R. G. Kostyanovskii
    • 1
  1. 1.Institute of Chemical PhysicsAcademy of Sciences of the USSRMoscow

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