Skip to main content
Log in

Dispersion of the optical rotation and circular dichroism in structural and stereochemical problems

Communication 2. The manifestation of chiral-optic effects in steroids of the pregnane series containing sulfur at C17

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

Conclusions

  1. 1.

    The chiral-optic properties of 17-sulfur-containing steroids of the pregnane series were investigated in the region of the p→π* transition of the 20-C=O and thiolacetate groups and the p→σ *5 transition of the C-S-C chromophore.

  2. 2.

    A 17α-substituent containing sulfur inverts the sign of the Cotton effect of the corresponding derivatives of Δ5-pregnene-3β-ol-20-one.

  3. 3.

    Considerations were expressed on the influence of substitution at C17 on the nature of the circular dichroism curves in the steroid series studied.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Literature cited

  1. A. A. Akhrem, T. K. Ustynyuk, G. A. Kogan, and V. A. Petukhov, Izv. Akad. Nauk SSSR, Ser. Khim., 377 (1971).

  2. P. Crabbé, Optical Rotatory Dispersion and Circular Dichroism in Organic Chemistry, San Francisco (1965).

  3. A. A. Akhrem, Z. I. Istomina, G. A. Kogan, A. I. Kuznetsova, and A. M. Turuta, Izv. Akad. Nauk SSSR, Ser. Khim., 2503 (1969).

  4. G. Snatzke (editor), Optical Rotatory Dispersion and Circular Dichroism in Organic Chemistry [Russian translation], Mir (1970), p. 361.

  5. K. Kuriyma, T. Komeno, and K. Takeda, Tetrahedron,22, 1039 (1969).

    Google Scholar 

  6. K. Takeda, K. Kuriyma, T. Komeno, D. A. Lightner, R. Records, and C. Djerassi, Tetrahedron,21, 1203 (1965).

    Google Scholar 

  7. K. W. Wellman and C. Djerassi, J. Amer. Chem. Soc.,87, 60 (1965).

    Google Scholar 

  8. C. Djerassi, J. Fornaguera, and O. Mancera, J. Amer. Chem. Soc.,81, 2383 (1959).

    Google Scholar 

  9. C. Djerassi, Optical Rotatory Dispersion [Russian translation], IL (1962), p. 166.

  10. L. Velluz, M. Legrand, and M. Grosjean, Optical Circular Dichroism [Russian translation], Mir (1967), p. 147.

  11. A. A. Akhrem, A. V. Kamernitskii, and A. V. Skorova, Izv. Akad. Nauk SSSR, Ser. Khim., 654 (1970).

  12. Tables of Interatomic Distances and Configuration in Molecules and Ions. Special Publ., No. 11, The Chem. Soc., London (1958).

  13. D. R. Hoff, J. Organ. Chem.,35, 2263 (1970).

    Google Scholar 

  14. G. Natanson, G. Winters, and A. A. Vigevani, Gaz. Chim. Ital.,95, 1359 (1965).

    Google Scholar 

  15. A. A. Akhrem, A. M. Turuta, G. A. Kogan, I. S. Kovnatskaya, and Z. I. Istomina, Izv. Akad. Nauk SSSR, Ser. Khim., 1454 (1972).

Download references

Author information

Authors and Affiliations

Authors

Additional information

For Communication 1, see [1].

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2688–2693, December, 1972.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Akhrem, A.A., Kogan, G.A., Turuta, A.M. et al. Dispersion of the optical rotation and circular dichroism in structural and stereochemical problems. Russ Chem Bull 21, 2620–2624 (1972). https://doi.org/10.1007/BF00849825

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00849825

Keywords

Navigation