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Influence of pressure on asymmetric synthesis

Communication 1. Diene condensation of di-(−)-menthyl fumarate with butadiene

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    The influence of pressure on asymmetric diene condensation of butadiene with di-(−)-menthyl fumarate was investigated. At atmospheric pressure (70°), the optical yield is equal to 0; at 5000 kg/cm2, an excess of the di-(−)-menthyl ester of (+)-Δ4-trans-cyclohexene-1,2-dicarboxylic acid is formed with an optical yield of 4.7%.

  2. 2.

    In the reaction studied, the transition state in the formation of the dimenthyl ester of the (+)-acid is characterized by lower values of the energy, entropy, and volume than in the case of the (−)-acid.

  3. 3.

    The role of the change in the free volume as a component of the volume effect of activation was discussed. It was concluded that there is a relationship between the steric hindrance of the reaction and the change in the free volume in the formation of the transition state.

  4. 4.

    Hypotheses are expressed on the principles of the influence of pressure on asymmetric synthesis.

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Literature cited

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Authors and Affiliations

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

    B. S. Él'yanov, E. I. Klabunovskii, M. G. Gonikberg, G. M. Parfenova & L. F. Godunova

Authors
  1. B. S. Él'yanov
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  2. E. I. Klabunovskii
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  3. M. G. Gonikberg
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  4. G. M. Parfenova
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  5. L. F. Godunova
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Additional information

A brief communication was published earlier [1].

Deceased.

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1658–1663, August, 1971.

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Él'yanov, B.S., Klabunovskii, E.I., Gonikberg, M.G. et al. Influence of pressure on asymmetric synthesis. Russ Chem Bull 20, 1557–1561 (1971). https://doi.org/10.1007/BF00860003

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  • DOI: https://doi.org/10.1007/BF00860003

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