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Effect of pressure on structural and steric orientation in diene synthesis Communication 1. Condensation of 1-vinylcyclopentene with methyl acrylate

  • Organic and Biological Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Summary

  1. 1.

    Increase in pressure from atmospheric to 6000 Kg/cm2 leads to a change in structural and steric orientation in the diene condensation of 1-vinylcyclopentene with methyl acrylate which favors the formation of the ortho-cis isomer. The relative amounts of the other three isomers scarcely change when pressure is applied.

  2. 2.

    For the analysis of the volume effects of activation in the system studied a cyclic transition state was assumed with a structure intermediate between that of a model with a parallel arrangement of the planes of the diene and dienophile, on the one hand, and the structure of the adduct, on the other. Such a transition state is in full accord with the experimental data obtained.

  3. 3.

    In the reaction studied the relative amounts of the stereoisomeric ortho adducts are determined mainly by electronic, not steric, effects.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences, USSR

    B. S. Él'yanov, B. A. Rudenko, M. G. Gonikberg & V. F. Kucherov

Authors
  1. B. S. Él'yanov
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  2. B. A. Rudenko
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  3. M. G. Gonikberg
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  4. V. F. Kucherov
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Setiya Khimicheskaya, No. 6, pp. 1082–1089, June, 1964

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Él'yanov, B.S., Rudenko, B.A., Gonikberg, M.G. et al. Effect of pressure on structural and steric orientation in diene synthesis Communication 1. Condensation of 1-vinylcyclopentene with methyl acrylate. Russ Chem Bull 13, 1003–1008 (1964). https://doi.org/10.1007/BF01141656

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  • DOI: https://doi.org/10.1007/BF01141656

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