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Stereochemistry of cyclic compounds Communication 24. Diene condensations of butadienyl acetate with maleic anhydride and with dimethyl fumarate, and the configurations of the resulting adducts

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Summary

  1. 1.

    The condensation of butadienyl acetate with maleic anhydride proceeds sterically selectively with formation of the cis-cis adduct (II), the configuration of which was proved by hydrogenation and lactonization.

  2. 2.

    In the condensation of butadienyl acetate with dimethyl fumarate both possible isomeric trans-trans and trans-cls adducts (XIV) and (XV) were isolated, and their configurations were proved by a study of their catalytic hydrogenation and hydrolysis and by an examination of molecular models.

  3. 3.

    Derivatives of the cis-cis and trans-cis series having an axial arrangement of the acetoxy group were found to be of low stability, and on catalytic hydrogenation, alkaline hydrolysis, and heating they lose acetic acid with formation of various cyclohexene-l,2-dicarboxylic acids. The isomeric compounds of the trans-transseries having an equatorial acetoxy group are fairly stable, so that some of their derivatives could be prepared.

  4. 4.

    By diene synthesis and catalytic hydrogenation, and in the study of the chemical reactions of the product, three of the theoretically possible four isomeric 3-acetoxy-l,2-cyclohexanedicarboxylic acids (VIII), (XXV), and (XXXII) and two isomeric trans-3-hydroxy-l,2-cyclohexanedicarboxylic acids (XXI) and (XXVIII) were obtained.

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Kucherov, V.F., Grigor'eva, N.Y. & Nazarov, I.N. Stereochemistry of cyclic compounds Communication 24. Diene condensations of butadienyl acetate with maleic anhydride and with dimethyl fumarate, and the configurations of the resulting adducts. Russ Chem Bull 8, 819–828 (1959). https://doi.org/10.1007/BF00915910

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Keywords

  • Hydrolysis
  • Adduct
  • Diene
  • Fumarate
  • Dicarboxylic Acid