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Pmr spectra and cis-trans isomerism of 2-methylenepyrrolidine and 2-methylenetetrahydrofuran derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A number of secondary enamines and cyclic enol ethers (2-methylenetetrahydrofuran derivatives) were synthesized by the reaction of O-methylbutyrolactim and 2,2-diethoxytetrahydrofuran, respectively, with compounds that have an active methylene link. The absence of reversible cis-trans isomerization was established in a study of the PMR spectra of these compounds. The configuration of the secondary enamines is determined by the possibility of the formation of a strong intramolecular hydrogen bond between the carbonyl-containing substituent and the NH group. In the case of the cyclic enol ethers it was shown that the energy barrier to cis-trans isomerization is greater than 25 kcal/mole and that, as a consequence of this, the geometrical isomers can be separated preparatively.

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Authors and Affiliations

  1. S. Ordzhonikidze All-Union Scientific-Research Institute of Pharmaceutical Chemistry, 119815, Moscow

    N. P. Solov'eva, N. B. Marchenko, V. G. Granik & Yu. N. Sheinker

Authors
  1. N. P. Solov'eva
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  2. N. B. Marchenko
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  3. V. G. Granik
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  4. Yu. N. Sheinker
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Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 914–918, July, 1982.

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Solov'eva, N.P., Marchenko, N.B., Granik, V.G. et al. Pmr spectra and cis-trans isomerism of 2-methylenepyrrolidine and 2-methylenetetrahydrofuran derivatives. Chem Heterocycl Compd 18, 693–696 (1982). https://doi.org/10.1007/BF00568944

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  • DOI: https://doi.org/10.1007/BF00568944

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