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

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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.

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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.

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    I. N. Nazarov, V. F. Kucherov and G. M. Segal', Bull. Acad. Sci. USSR, Div. Chem. Sci., 1956, 559.

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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).

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    I. N. Nazarov, V. F. Kucherov and G. M. Segal', Bull. Acad. Sci. USSR, Div. Chem. Sci., 1956, 1215.

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    I. N. Nazarov, V. F. Kucherov and V. M. Andreev, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1956, 951.

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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).

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Kucherov, V.F., Segal', G.M. & Nazarov, I.N. Stereochemistry of cyclic compounds Communication 23. Stereochemistry of oxidation of anti-Δ4-octalin-1-carboxylic acid. Russ Chem Bull 8, 652–658 (1959). https://doi.org/10.1007/BF00915860

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Keywords

  • Oxidation
  • Methyl
  • Glycol
  • Carboxyl
  • Anhydride