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Stereochemistry of cyclic compounds

Communication 25. Condensation of trans-3-methyl-1,3-pentadiene with maleic anhydride. synthesis and configurations of the four isomers of 3,4-dimethyl-4-cyclohexene-l,2-dicarboxylic acid

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

Summary

  1. 1.

    A study was made of the diene condensation of trans-3-methyl-1,3-pentadiene with maleic anhydride, which proceeds sterically selectively with formation of the cis-cis anhydride (IV), by the thermal isomerization of which the isomeric cis-trans anhydride (VII) was obtained.

  2. 2.

    With the aid of stereospecific isomerization reactions of the corresponding monoesters, we prepared all four theoretically possible stereoisomers of 3,4-dimethyl-4-cyclohexene-1,2-dicarboxylic acid (V), (VIII), (XI), and (XIV), the configurations of which were proved by their lactonization.

  3. 3.

    In the study of the steric course of the lactonization of the isomeric cis-trans and trans-cis acids (VIII) and (XIV), it was proved that conformations resulting from the rotational isomerism of the cyclohexane ring take part in these reactions.

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Literature cited

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Authors and Affiliations

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

    V. F. Kucherov, V. M. Andreev & I. N. Nazarov

Authors
  1. V. F. Kucherov
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  2. V. M. Andreev
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  3. I. N. Nazarov
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Kucherov, V.F., Andreev, V.M. & Nazarov, I.N. Stereochemistry of cyclic compounds. Russ Chem Bull 8, 1022–1030 (1959). https://doi.org/10.1007/BF00916670

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  • DOI: https://doi.org/10.1007/BF00916670

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