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Transformed steroids

29. Anomalous reaction of Δ5,l6-pregnadienol-3β-one-20 3-acetate with potassium thiocyanate in acetic acid

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

Conclusions

  1. 1.

    We detected an unusual reaction between Δ5,16-pregnadienol-3β-one-20 3-acetate and potassium thiocyanate in acetic acid at 100°, yielding 16α-thiol-Δ5-pregnenol-3β-one-20 3,16-diacetate.

  2. 2.

    A new method was devised for synthesis of 16α-thiol-Δ5-pregnenol-3β-one-20 3,16-diacetate, based on the anomalous reaction of dehydropregnenolone acetate with potassium thiocyanate.

  3. 3.

    It was established for the first time that 16α-isothiocyan-Δ5-pregnenol-3β-one-20 is converted to 16α-thiol-Δ5-pregnenol-3β-one-20 3,16-diacetate when heated with potassium acetate in acetic acid.

  4. 4.

    We have discussed the probable mechanism of the reactions studied.

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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, Z. I. Istomina, A. I. Kuznetsova & A. M. Turuta

Authors
  1. A. A. Akhrem
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  2. Z. I. Istomina
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  3. A. I. Kuznetsova
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  4. A. M. Turuta
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Additional information

For 28, see [1].

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2073–2078, September, 1970.

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Akhrem, A.A., Istomina, Z.I., Kuznetsova, A.I. et al. Transformed steroids. Russ Chem Bull 19, 1947–1950 (1970). https://doi.org/10.1007/BF00849778

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  • DOI: https://doi.org/10.1007/BF00849778

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