Advertisement

Chemistry of Heterocyclic Compounds

, Volume 15, Issue 5, pp 498–501 | Cite as

Mechanism of the ring-chain tautomerism of 2,3,3-trimethyl-2-hydroxy-5-pyrrolidones

  • L. Yu. Yuzefovich
  • B. M. Sheiman
  • V. G. Mairanovskii
  • T. M. Filippova
Article
  • 31 Downloads

Abstract

The mechanism of the prototropic equilibrium process of ring-chain tautomerization of 2,3,3-trimethyl-2-hydroxy-5-pyrrolidones is discussed on the basis of the results obtained by PMR spectroscopy. On the NMR time scale the reaction proceeds with the formation of a common intermediate anion, and the rate-determining step is the detachment of a proton.

Keywords

Spectroscopy Organic Chemistry Equilibrium Process Intermediate Anion Prototropic Equilibrium 
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.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    M. I. Kabachnik, Zh. Vses. Khim. Ova.,7, 263 (1962).Google Scholar
  2. 2.
    K. Bowden and F. A. El Kaissi, J. Chem. Soc., Perkin Trans. II, No. 14, 1927 (1977).Google Scholar
  3. 3.
    B. M. Sheiman, L. Yu. Yuzefovich, L. Ya. Denisova, T. M. Filippova, V. G. Mairanovskii, and V. M. Berezovskii, Khim. Geterotsikl. Soedin., No. 5, 634 (1977).Google Scholar
  4. 4.
    L. Yu. Yuzefovich, B. M. Sheiman, T. M. Filippova, and V. G. Mairanovskii, Khim. Geterotsikl. Soedin., No. 6, 758 (1978).Google Scholar
  5. 5.
    C. D. Johnson, Hammett Equation, Cambridge University Press (1973).Google Scholar
  6. 6.
    H. Watary and N. Suzuki, J. Inorg. Nucl. Chem.,36, 1815 (1974).Google Scholar
  7. 7.
    B. M. Sheiman, L. Ya. Denisova, S. F. Dymova, and V. M. Berezovskii, Khim. Geterotsikl. Soedin., No. 5, 787 (1975).Google Scholar

Copyright information

© Plenum Publishing Corporation 1979

Authors and Affiliations

  • L. Yu. Yuzefovich
    • 1
  • B. M. Sheiman
    • 1
  • V. G. Mairanovskii
    • 1
  • T. M. Filippova
    • 1
  1. 1.All-Union Scientific-Research Vitamin InstituteMoscow

Personalised recommendations