Chemistry of Heterocyclic Compounds

, Volume 23, Issue 9, pp 951–953 | Cite as

Condensation reactions involving the α-methylene group in series of 5-alkylpyrrolidine-2-thiones and 5-alkyl-1-acetyl-2-pyrrolidones

  • G. V. Bespalova
  • V. A. Sedavkina
  • V. G. Kharchenko
  • A. D. Shebaldova
  • V. I. Labunskaya
Article

Abstract

It is shown that 1-substituted and N-unsubstituted 5-R-pyrrolidine-2-thiones, in contrast to their oxygen analogs, undergo methylenethioalkylation and the Mannich and Michael reactions at the 3 position of the ring; this is due to their higher CH acidity. The results of quantum-chemical calculations (by the MO LCAO method within the CNDO/2 approximation) confirm the similar reactivities of pyrrolidine-2-thiones and 1-acetyl-substituted 2-pyrrolidones.

Keywords

Oxygen Organic Chemistry Acidity Condensation Reaction Similar Reactivity 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature Cited

  1. 1.
    G. V. Bespalova, V. A. Sedavkina, and V. A. Kharchenko, Khim. Geterotsikl. Soedin., No. 12, 1648 (1979).Google Scholar
  2. 2.
    G. V. Bespalova, V. A. Sedavkina, and V. A. Kharchenko, Khim. Geterotsikl. Soedin., No. 3, 404 (1981).Google Scholar
  3. 3.
    A. I. Kitaigorodskii, P. M. Zorkii, and V. K. Belen'kii, Structures of Organic Substances. Data from Structural Investigations 1929–1970 [in Russian], Nauka, Moscow (1980), p. 284.Google Scholar
  4. 4.
    V. A. Sedavkina and G. V. Bespalova, Khim. Geterotsikl. Soedin., No. 3, 333 (1972).Google Scholar

Copyright information

© Plenum Publishing Corporation 1988

Authors and Affiliations

  • G. V. Bespalova
    • 1
  • V. A. Sedavkina
    • 1
  • V. G. Kharchenko
    • 1
  • A. D. Shebaldova
    • 1
  • V. I. Labunskaya
    • 1
  1. 1.N. G. Chernyshevskii Saratov State UniversitySaratov

Personalised recommendations