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Corticosteroid analogs

Communication 21. Stereochemistry of the opening of stereoisomeric 1-acetyl-4-t-butyl-1,2-epoxycyclohexanes in presence of ethyl carbazate

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    The stereochemistry of the opening of the steroisomeric 1-acetyl-4-t-butyl-l,2-epoxycyclohexanes in presence of ethyl carbazate was studied. The opening of the epoxides is preceded by the formation of the (ethoxycarbonyl)hydrazones of the epoxy ketones.

  2. 2.

    In presence of ethyl carbazate in acetic acid the 1α,2α-epoxide undergoes cis-opening exclusively, but in aqueous dioxane cis-opening is accompanied by the trans-diaxial opening of the epoxide ring.

  3. 3.

    In presence of ethyl carbazate, both in acetic acid and in aqueous dioxane in presence of sulfuric acid, the 1β,2β-epoxide undergoes mainly trans-diequatorial opening, but also some cis-opening of the epoxide ring occurs.

  4. 4.

    It was shown that preferential equatorial entry of a substituent at the C1 reaction center occurs in the ring-opening of (ethoxycarbonyl)hydrazones of the stereoisomeric epoxy ketones.

  5. 5.

    The probable mechanism of the opening of epoxy ketones in presence of ethyl carbazate is discovered.

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Literature cited

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  3. A. A. Akhrem, A. V. Kamernitskii, V. A. Dubrovskii, and A. M. Moiseenkov, Izv. AN SSSR, Ser. Khim.,1964, 1726.

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Authors and Affiliations

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

    V. N. Dobrynin & A. A. Akhrem

Authors
  1. V. N. Dobrynin
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  2. A. A. Akhrem
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 1969–1974, November, 1966.

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Dobrynin, V.N., Akhrem, A.A. Corticosteroid analogs. Russ Chem Bull 15, 1902–1906 (1966). https://doi.org/10.1007/BF01179700

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  • DOI: https://doi.org/10.1007/BF01179700

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