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Corticosteroid analogs Communication 15. Reactions of 1-acetyl-1-bromo-2-cyclohexanol and its acetate with carbazic ester

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

Summary

  1. 1.

    The reaction of the bromohydrin acetate (I) with carbazic ester goes stereospecifically, like its acetolysis, and leads to the cis acetate hydrazone (III) with inversion of configuration.

  2. 2.

    About 30% of the products of the analogous reaction of the bromohydrin (II) have the configuration of the starting compound. It is considered that these products arise as a result of the reaction of the bromohydrin (II) in the diequatorial conformation, whereas under these conditions the diaxial conformer gives products of inverted configuration.

  3. 3.

    The isolation of the monoacetates (III), (V), (VII), and (IX) from the reaction products indicates the high stability of the secondary acetoxy group, as compared with the tertiary, and therefore the occurrence of acyl migration in the 1-acetyl-1,2-cyclohexanediol series.

  4. 4.

    The probable mechanism of the transformations observed is discussed.

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Literature cited

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Authors and Affiliations

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

    A. A. Akhrem & A. M. Moiseenkov

Authors
  1. A. A. Akhrem
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  2. A. M. Moiseenkov
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2161–2167, December, 1966.

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Akhrem, A.A., Moiseenkov, A.M. Corticosteroid analogs Communication 15. Reactions of 1-acetyl-1-bromo-2-cyclohexanol and its acetate with carbazic ester. Russ Chem Bull 15, 2092–2096 (1966). https://doi.org/10.1007/BF00867706

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  • DOI: https://doi.org/10.1007/BF00867706

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