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Stereochemistry of cyclic compounds Communication 23. Stereochemistry of oxidation of anti-Δ4-octalin-1-carboxylic acid

  • V. F. Kucherov
  • G. M. Segal'
  • I. N. Nazarov
Article
  • 19 Downloads

Summary

  1. 1.

    The stereochemistry of oxidation of anti-Δ4-octalin-1-carboxylic acid (IV) with peracetic acid and osmic anhydride was studied.

     
  2. 2.

    On the basis of the study of stereospecific reactions and of the examination of molecular models, it was shown that the oxidation in both instances proceeds from the side that is opposite to the equatorial carboxyl group, which permits one to prepare the α-oxide (V) and the isomeric glycols of trans-decalin series (VII) and (XII).

     
  3. 3.

    The condensation of trans-1,2-dimethylbutadiene with methyl acrylate was accomplished and the configuration of the resulting cis-adduct (XXI) was proved by lactonization and oxidation with peracetic acid.

     

Keywords

Oxidation Methyl Glycol Carboxyl Anhydride 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Literature cited

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    V. F. Kucherov, G. M. Segal' and I. N. Nazarov, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1959, 673.Google Scholar
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    I. N. Nazarov, V. F. Kucherov and G. M. Segal', Bull. Acad. Sci. USSR, Div. Chem. Sci., 1956, 559.Google Scholar
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    D. Barton, J. Chem. Soc. 1953, 1027; I. N. Nazaroy and L. D. Bergel'son, Progr. Chem. (USSR) 26, 3 (1957).Google Scholar
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    I. N. Nazarov, V. F. Kucherov and G. M. Segal', Bull. Acad. Sci. USSR, Div. Chem. Sci., 1956, 1215.Google Scholar
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    I. N. Nazarov, V. F. Kucherov and V. M. Andreev, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1956, 951.Google Scholar
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    I. N. Nazarov, A. I. Kuznetsova and N. V. Kuznetsov, J. Gen. Chem. 25, 88 (1955); P. Abelmann. Ber. 43, 1574 (1910).Google Scholar

Copyright information

© Consultants Bureau Enterprises Inc 1960

Authors and Affiliations

  • V. F. Kucherov
    • 1
  • G. M. Segal'
    • 1
  • I. N. Nazarov
    • 1
  1. 1.N. D. Zelinskii Institute of Organic Chemistry of the Academy of SciencesUSSR

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