Monatshefte für Chemie / Chemical Monthly

, Volume 106, Issue 3, pp 679–693 | Cite as

Zum Verhalten von Olefinen, konjugierten Dienen und Steroidolefinen gegenüber Pb(OCOCF3)4

  • Dietmar Westphal
  • Erich Zbiral
Organische Chemie und Biochemie

Reactions of Pb(OCOCF3)4 with olefines, conjugated dienes and steroid olefines

Abstract

The reaction of Pb(OCOCF3)4 with several olefines and conjugated dienes is reported. The oxidation of styrene, stilbene and 1.4-dihydro-1.4-methanonaphthalene leads to phenylacetaldehyde (1), benzaldehyde (2) and benzophenone (3), and to 1.2.3.4-tetrahydro-1.4-methanonaphthalene-(2S,9R+2R,9S)-diol-bis-trifluoroacetate (8) respectively. Of the conjugated dienes, 1.3-cyclohexadiene yieldscis-2-cyclohexene-1.4-diol bis-trifluoroacetate (4), cyclopentadiene yieldscis-2-cyclopentene-1.4-diolbis-trifluoroacetate (5) andtrans-2-cyclopentene-1.4-diol-bis-trifluoroacetate (6) andE,E-2.4-hexadiene yields the isomers of 3-hexene-2.5-diol bis trifluoroacetate (7). Oxidation of unsaturated steroids such as 2-cholestene, 2-androsten-17-one, 4-cholestene, androsta-4.9(11)-diene-3.17-dione and 3β-acetoxy-5-cholestene results in cholestane-2α,3α-diol diacetate (9), 2α,3α-diacetoxyandrostan-17-one (10) and 1α-acetoxy-2-androsten-17-one (11), in coprostane-4β,5β-diol-4β-trifluoroacetate (12) or coprostane 4β,5β-diol-4β-acetate (12a), 4-cholestanone (13), in 12α-trifluoroacetoxyandrosta-4,9(11)-diene-3.17-dione (14), and in cholestane-3β,5α,6α-triol-3β-acetate-6α-trifluoracetate.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literatur

  1. 1.
    R. E. Partch, J. Amer. Chem. Soc.89, 3662 (1967).Google Scholar
  2. 2.
    J. R. Campbell, J. R. Kalman, J. T. Pinhey undS. Sternhell, Tetrahedron Lett.18, 1763 (1972).Google Scholar
  3. 3.
    J. R. Kalman, J. T. Pinhey undS. Sternhell, Tetrahedron Lett.52, 5369 (1972).Google Scholar
  4. 4.
    D. Westphal undE. Zbiral, im Druck.Google Scholar
  5. 5.
    F. Huber undM. S. A. El-Meligy, Z. anorg. allg. Chem.399 349 (1973).Google Scholar
  6. 6.
    K. B. Wiberg, Oxidation in Organic Chemistry, Vol. 5-A. New York-London: Acad. Press, und hieraus angeführte Referenzen.Google Scholar
  7. 7.
    G. E. Heasley, V. L. Heasley, S. L. Manatt, H. A. Day, R. V. Hodges, P. A. Kroon, D. A. Redfield, T. L. Rold undD. E. Williamson, J. Org. Chem.38, 4109 (1973).Google Scholar
  8. 8a.
    K. Alder, F. Flock undH. Wirtz, Chem. Ber.91, 609 (1958).Google Scholar
  9. 8b.
    J. Meinwald undG. A. Wiley, J. Amer. Chem. Soc.80, 3667 (1958).Google Scholar
  10. 9.
    H. B. Henbest undM. Smith, J. Chem. Soc. [London]1957, 926.Google Scholar
  11. 10a.
    J. F. Eastham, G. B. Miles undC. H. Krauth, J. Amer. Chem. Soc.81, 3114 (1959).Google Scholar
  12. 10b.
    D. Lavie, Y. Kashman undE. Glotter, Tetrahedron22, 1103 (1966).Google Scholar
  13. 11.
    D. H. R. Barton undW. J. Rosenfelder, J. Chem. Soc.1951, 1048.Google Scholar
  14. 12.
    E. Zbiral undH. Hugl, Tetrahedron29, 769 (1973).Google Scholar
  15. 13.
    V. Schwarz undS. Hermanek, Collect. Czech. Chem. Commun.29, 2360 (1964).Google Scholar
  16. 14.
    V. Prelog undE. Tagmann, Helv. chim. Acta27, 1867 (1944).Google Scholar

Copyright information

© Springer-Verlag 1975

Authors and Affiliations

  • Dietmar Westphal
    • 1
  • Erich Zbiral
    • 1
  1. 1.Organisch-Chemischen Institut der Universität WienWienÖsterreich

Personalised recommendations