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Corticosteroid analogs Communication 14. Behavior of the secondary acetoxy group in the acetylcyclohexanediol series

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

Summary

  1. 1.

    A study was made of the hydrolysis of cis- and trans-1-acetyl-1,2-cyclohexanediol diacetates in alkaline and acid conditions. The hydrolysis of the 1,2-diacetates probably pass through the intermediate formation of tertiary monoacetates with subsequent intramolecular migration of acetyl and finally hydrolysis of the secondary monoacetates formed into the corresponding diols.

  2. 2.

    In the hydrolysis of the trans-diol diacetate (II) under acid conditions, as well as the trans monoacetate (V) and the trans-diol (VI), a compound of unestablished structure is formed; this is close in R f value to the trans acetate (V), and when it is kept it is gradually converted into (V).

  3. 3.

    The acetolysis of trans-1-acetyl-1-bromo-2-cyclohexanol acetate, which was prepared for the first time, probably goes via the formation of an intermediate cyclic orthoacetate and is accompanied by the removal of the bromine atom with inversion of configuration by a mechanism of intramolecular SN2 substitution.

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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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Additional information

Translated from Izveztiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2156–2161, December, 1966.

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Akhrem, A.A., Moiseenkov, A.M. Corticosteroid analogs Communication 14. Behavior of the secondary acetoxy group in the acetylcyclohexanediol series. Russ Chem Bull 15, 2087–2091 (1966). https://doi.org/10.1007/BF00867705

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  • DOI: https://doi.org/10.1007/BF00867705

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