Structure and reactivity in steroids

Communication 3. Kinetics of the oxidation of derivatives of 3,17β-estradiol and D-3,17αβ-homoestradiol
  • V. V. Egorova
  • A. V. Zakharychev
  • S. N. Ananchenko
  • I. V. Torgov
Physical Chemistry


  1. 1.

    An analysis was made of a previously proposed mechanism of the oxidation of secondary alcohols by CrO3 in CH3COOH; a formula was derived for the rate of this conversion under equilibrium conditions, and it was shown that the reactivity of the substrates can be characterized by two constants: thermodynamic and kinetic.

  2. 2.

    The kinetics of the oxidation of the 17β-OH group of derivatives of 3,17β-estradiol, D-3,17αβ-homoestradiol was studied, and it was shown that the experimental data satisfy the equation obtained.

  3. 3.

    A relationship was established between the reactivity of the 17β- and 17αβ-OH groups of estrogens as a function of the size of the D ring, the coupling of the B and C rings, and the electronic character of the substituent at C3.



Oxidation Alcohol Experimental Data Steroid Estrogen 
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Literature cited

  1. 1.
    L. Vellus, J. Valls, and G. Nomine, Angew. Chemie,77, 185 (1965).Google Scholar
  2. 2.
    D. H. R. Barton, A. J. Head, J. Chem. Soc., 932 (1956); D. H. R. Barton, A. J. Head, and P. J. May, J. Chem. Soc., 935 (1957).Google Scholar
  3. 3.
    D. H. R. Barton, Experientia,6, 316 (1960).Google Scholar
  4. 4.
    D. H. R. Barton, F. Mc. Capra, P. J. May, and F. Thudium, J. Chem. Soc., 1297 (1960).Google Scholar
  5. 5.
    O. H. Wheeler and J. L. Mateos, Canad. J. Chem.,36, 712 (1958);36, 1735 (1958).Google Scholar
  6. 6.
    R. Bucourt, Bull. Soc. Chim. France, 2081 (1964).Google Scholar
  7. 7.
    M. J. T. Robinson and W. B. Whalley, Tetrahedron,19, 2123 (1963).Google Scholar
  8. 8.
    V. Schwarz, S. Hermanek, and J. Trojanek, Chem. Industr., 1212 (1960).Google Scholar
  9. 9.
    V. Schwarz, S. Hermanek, and J. Trojanek, Coll. Czechosl. Chem. Comm.,27, 2778 (1962).Google Scholar
  10. 10.
    V. Schwarz and S. Hermanek, Tetrahedron Letters, 809 (1962); Coll. Czechosl. Chem. Comm.,29, 2360 (1964).Google Scholar
  11. 11.
    P. E. Peterson, Tetrahedron Letters, 181 (1963).Google Scholar
  12. 12.
    J. Mathieu, M. Legrand, and J. Valls, Bull. Soc. Chim. France, 549 (1960).Google Scholar
  13. 13.
    M. Legrand, V. Delaroff, and J. Mathieu, Bull. Soc. Chim. France, 1346 (1961).Google Scholar
  14. 14.
    J. Orr, P. Carter, and L. L. Engel, Biochemistry,6, 1065 (1967).PubMedGoogle Scholar
  15. 15.
    V. V. Egorova, S. N. Ananchenko, A. V. Zakharychev, and I. V. Torgov, Izv. Akad. Nauk SSSR, Ser. Khim., 943 (1969).Google Scholar
  16. 16.
    K. B. Wiberg, Oxidation in Organic Chemistry,5A, Ch. 11, Academic Press, New York-London (1965), p. 69.Google Scholar
  17. 17.
    K. B. Wiberg and H. Schafer, J. Amer. Chem. Soc.,89, 455 (1967);91, 927 (1969);91, 933 (1969).Google Scholar
  18. 18.
    J. Schreiber and A. Eschenmoser, Helv. Chim. Acta,38, 1529 (1955).Google Scholar
  19. 19.
    L. M. Batuner and M. E. Pozin, Mathematical Methods in Chemical Technology [in Russian], Goskhimizdat, Leningrad (1963).Google Scholar
  20. 20.
    D. G. Lee, W. L. Downey, and R. M. Maass, Canad. J. Chem.,46, 441 (1968).Google Scholar
  21. 21.
    L. Fieser and M. Fieser, Steroids [Russian translation], IL (1964), p. 476.Google Scholar
  22. 22.
    T. Miki, K. Higaro, and T. Asako, Chemical Pharm. Bull.,13, 1285 (1965).Google Scholar
  23. 23.
    V. E. Limanov, S. N. Ananchenko, and I. V. Torgov, Izv. Akad. Nauk SSSR, Ser. Khim., 1814 (1964).Google Scholar
  24. 24.
    K. K. Koshoev, S. N. Ananchenko, and I. V. Torgov, Khimiya Prirodn. Soed.,3, 172 (1965).Google Scholar
  25. 25.
    V. M. Rzheznikov, S. N. Ananchenko, and I. V. Torgov, Khimiya Prirodn. Soed.,2, 90 (1965).Google Scholar

Copyright information

© Consultants Bureau 1971

Authors and Affiliations

  • V. V. Egorova
    • 1
  • A. V. Zakharychev
    • 1
  • S. N. Ananchenko
    • 1
  • I. V. Torgov
    • 1
  1. 1.Institute of the Chemistry of Natural CompoundsAcademy of Sciences of the USSRUSSR

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