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Stereochemistry of cyclic compounds

Communication 54. Stereochemistry of the addition of hypobromous acid to the sodium salts of cis-4-cyclohexene-1,2-dicarboxylic acid and of its monoester

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

Summary

  1. 1.

    The bromination of the sodium salt of cis-4-cyclohexene-1,2-dicarboxylic acid (IV) was studied, and the spatial structure of the bromo γ-lactone acid (V) formed in this reaction was proved.

  2. 2.

    A possible reaction scheme was examined for the bromination of the sodium salt of cis-4-cyclohexene-1, 2-dicarboxylic monoester (XI), which probably proceeds via isomeric carbonium ions.

  3. 3.

    It was confirmed that the β-configuration is to be assigned to the epoxy anhydride (XVII) formed by the action of peroxyacetic acid on cis-4-cyclohexene-1,2-dicarboxylic anhydride.

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

Authors
  1. A. S. Onishchenko
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  2. A. L. Shabanov
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  3. V. F. Kucherov
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Onishchenko, A.S., Shabanov, A.L. & Kucherov, V.F. Stereochemistry of cyclic compounds. Russ Chem Bull 12, 770–773 (1963). https://doi.org/10.1007/BF01134722

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  • DOI: https://doi.org/10.1007/BF01134722

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