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Synthesis of di- and tetrahydropyrroles.

XII. Effect of substituents attached to the nitrogen atom, solvents, and temperature on the ring-chain tautomerism of substituted 2-hydroxy-5-pyrrolidones

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

It was established by means of PMR spectroscopy that the ring-chain tautomeric equilibrium in solutions of 2,3,3-trimethyl-2-hydroxy-5-pyrrolidone and its N-substituted erivatives is shifted exclusively or primarily to favor the cyclic form and that the nature of the solvent has little effect on the position of the equilibrium. An increase in the temperature or the electron-acceptor character of the substituent attached to the nitrogen atom promotes an increase in the percentage of the open forms. The time required to establish the tautomeric equilibrium was determined.

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Literature cited

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Authors and Affiliations

  1. All-Union Scientific-Research Vitamin Institute, Moscow

    B. M. Sheiman, L. Ya. Denisova, S. F. Dymova & V. M. Berezovskii

Authors
  1. B. M. Sheiman
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  2. L. Ya. Denisova
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  3. S. F. Dymova
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  4. V. M. Berezovskii
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Additional information

See [1] for communication XI.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 787–791, June, 1975.

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Sheiman, B.M., Denisova, L.Y., Dymova, S.F. et al. Synthesis of di- and tetrahydropyrroles.. Chem Heterocycl Compd 11, 685–689 (1975). https://doi.org/10.1007/BF00959962

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  • DOI: https://doi.org/10.1007/BF00959962

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