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


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.


Spectroscopy Ester Organic Chemistry Dehydration Equilibrium Position 
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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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