Stereoselectivity of hydrosilylation of olefins

  • A. V. Podol'skii
  • T. G. Cherezova
  • V. P. Kachalkov
  • M. I. Kodess
Brief Communications


It was discovered that disubstituted olefins, in which the double bond is conjugated with an aromatic system, exhibit stereoselective hydrosilylation: only the trans isomers react directly. The hydrosilylation of the cis isomers is accomplished via prior conversion to the trans isomers. It was postulated that the stereoselectivity of the process is based on the trans-addition mechanism.


Double Bond Trans Isomer Aromatic System Prior Conversion Disubstituted Olefin 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    R. A. Benkeser, Pure Appl. Chem.,13, 133 (1966).Google Scholar
  2. 2.
    M. Capka, P. Svoboda, V. Bazant, and V. Chvalovsky, Chem. Prumysl,21, 324 (1971).Google Scholar
  3. 3.
    J. V. Swisher and C. Zullig, J. Org. Chem.,38, 3353 (1973).Google Scholar
  4. 4.
    M. C. Musolf and J. L. Speier, J. Org. Chem.,29, 2519 (1964).Google Scholar
  5. 5.
    A. I. Nogaideli, L. I. Nakaidze, and V. S. Tskhovrebashvili, Zh. Obshch. Khim.,44, 1763 (1974).Google Scholar
  6. 6.
    C. S. Cundy, B. M. Kingston, and M. F. Lappert, Advances Organomet. Chem.,11, 297 (1973).Google Scholar
  7. 7.
    F. Conti, L. Raimondi, G. F. Pregaglia, and R. Ugo, J. Organomet. Chem.,70, 107 (1974).Google Scholar
  8. 8.
    A. V. Podol'skii, T. G. Cherezova, and M. A. Bulatov, Zh. Obshch. Khim.,47, 1527 (1977).Google Scholar
  9. 9.
    R. Ya. Levina, L. E. Karelova, and I. A. El'yashberg, Zh. Obshch. Khim.,10, 913 (1940).Google Scholar
  10. 10.
    R. Y. Mixer, R. F. Heck, S. Winstein, and W. G. Young, J. Am. Chem. Soc.,75, 4094 (1953).Google Scholar
  11. 11.
    G. Wittig and W. Haag, Chem. Ber.,88, 1654 (1955).Google Scholar

Copyright information

© Plenum Publishing Corporation 1979

Authors and Affiliations

  • A. V. Podol'skii
    • 1
  • T. G. Cherezova
    • 1
  • V. P. Kachalkov
    • 1
  • M. I. Kodess
    • 1
  1. 1.Institute of ChemistryUral Scientific Center of the Academy of Sciences of the USSRSverdlovsk

Personalised recommendations