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Chemistry of Heterocyclic Compounds

, Volume 9, Issue 1, pp 18–21 | Cite as

Syntheses of di- and tetrahydropyrroles

IX. Dehydration and ring-chain tautomerism of 2,3,3-trimethyl-2-hydroxy-5-pyrrolidones
  • B. M. Sheiman
  • L. Ya. Denisova
  • S. F. Dymova
  • V. M. Berezovskii
Article
  • 21 Downloads

Abstract

It is shown by means of IR and PMR spectra that the products of the aminolysis of esters of 3,3-dimethyl(2-carbethoxy)levulinic acid and γ-chloro-β,β,γ-trimethylbutyrolactone exist in the cyclic form of 2-hydroxy-5-pyrrolidones (Ia-d). It was established by PMR spectroscopy that, except for the 4-carbamido derivative (Id), these compounds undergo spontaneous dehydration in anhydrous solutions. In addition, ring-chain tautomeric equilibrium is established in solutions of the N-phenyl derivative (Ib). The rates of establishment of equilibrium and the equilibrium positions were investigated for both processes.

Keywords

Spectroscopy Ester Organic Chemistry Dehydration Equilibrium Position 
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.

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Copyright information

© Consultants Bureau, a division of Plenum Publishing Corporation 1975

Authors and Affiliations

  • B. M. Sheiman
    • 1
  • L. Ya. Denisova
    • 1
  • S. F. Dymova
    • 1
  • V. M. Berezovskii
    • 1
  1. 1.All-Union Scientific-Research Vitamin InstituteUSSR

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