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Stereochemistry of cyclic compounds Communication 62. Stereochemistry of the oxidation of 4-methyl-4-cyclohexene-1,2-dicarboxylic anhydride

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

Summary

The stereochemistry of the oxidation of 4-methyl-4-cyclohexene-1,2-dicarboxylic anhydride with peroxyacetic acid was studied, and by a series of transformations it was proved that the epoxide then formed has the ßconfiguration. The observed stereospecificity of the oxidation is explained on the basis of views on a predominant boat conformation for 4-cyclohexane-1,2-dicarboxylic anhydrides.

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Literature cited

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Authors and Affiliations

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

    A. L. Shabanov, A. S. Onishchencko & V. F. Kucherov

Authors
  1. A. L. Shabanov
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  2. A. S. Onishchencko
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  3. V. F. Kucherov
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Additional information

This article is published in accordance with a resolution of the Conference of Chief Editors of the Journals of the Academy of Sciences of the USSR, July 12, 1962, as a dissertation paper by A. L. Shabanov.

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Shabanov, A.L., Onishchencko, A.S. & Kucherov, V.F. Stereochemistry of cyclic compounds Communication 62. Stereochemistry of the oxidation of 4-methyl-4-cyclohexene-1,2-dicarboxylic anhydride. Russ Chem Bull 12, 1643–1647 (1963). https://doi.org/10.1007/BF00845793

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  • DOI: https://doi.org/10.1007/BF00845793

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