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Stereochemistry of cyclic compounds Communication 13. Synthesis and stereochemistry of isomeric decaftydro-1,2-naphthalenedicarboxylic acids

  • Organic and Biological Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Summary

  1. 1.

    Six of the eight theoretically possible isomers of decahydro-1,2-naphthalenedicarboxylic acid (I), (II), (VI), (X), (XIV), and (XX) are described, and in each case a rigorous determination of spatial configuration is made.

  2. 2.

    A study is made of the chemical transformations of all the synthesized isomeric decahydro-1,2-naphtha - lenedicarboxylic acids and of the cis-trans isomerization of the corresponding mono- and di-esters in presence of sodium methoxide. It is shown th t the isomers obtained are relatively stable both to heat and to alkaline reagents.

  3. 3.

    On the basis of the theory of equatorial-polar bonds in the cyclohexane molecule and of an examination of molecular models, all the peculair features of the mutual transofrmations of the six isomeric decahydroacids and their esters can be explained.

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Authors and Affiliations

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

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

Authors
  1. N. Nazarov
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  2. V. F. Kucherov
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  3. V. M. Andreev
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Nazarov, N., Kucherov, V.F. & Andreev, V.M. Stereochemistry of cyclic compounds Communication 13. Synthesis and stereochemistry of isomeric decaftydro-1,2-naphthalenedicarboxylic acids. Russ Chem Bull 5, 1107–1117 (1956). https://doi.org/10.1007/BF01177364

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  • DOI: https://doi.org/10.1007/BF01177364

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