Direct metallation of cyclic conjugated hydrocarbons by highly reactive magnesium

  • U. M. Dzhemilev
  • A. G. Ibragimov
  • E. V. Gribanova
  • L. M. Khalilov
Organic Chemistry

Conclusions

Organomagnesium compounds have been prepared by the direct metallation of cyclopentadiene, indene, fluorene, and cyclooctatetraene and by highly reactive magnesium. Their crosscombination with allyl and propargyl electrophiles in the presence of metal complex catalysts has been studied, this leading to the allyl and propargyl substituted hydrocarbons being obtained in high yields.

Keywords

Indene Magnesium Hydrocarbon Fluorene Metal Complex 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    R. D. Rieke and P. M. Hudnall, J. Am. Chem. Soc.,94, 178 (1972).Google Scholar
  2. 2.
    R. D. Rieke and S. E. Bales, J. Chem. Soc, Chem. Commun., 879 (1973).Google Scholar
  3. 3.
    R. D. Rieke and S. E. Bales, J. Am. Chem. Soc.,96, 775 (1974).Google Scholar
  4. 4.
    R. D. Rieke, Accounts Chem. Res.,10, 301 (1977).Google Scholar
  5. 5.
    R. D. Salomon, J. Org. Chem.,39, 602 (1974).Google Scholar
  6. 6.
    A. M. Moiseenkov, B. A. Czeskis, and A. V. Semenovsky, Tetrahedron Lett., 853 (1980).Google Scholar
  7. 7.
    A. A. Cheskis (Czeskis), A. M. Moiseenkov, M. I. Struchkova, and A. V. Semenovskii (Semenovsky), Izv. Akad. Nauk SSSR, Ser Khim., 365 (1981).Google Scholar
  8. 8.
    T. Saito, J. Chem. Soc, Chem. Commun., 1422 (1971).Google Scholar
  9. 9.
    E. A. Chernyshev, M. D. Reshetova, and I. A. Rodnikov, Zh. Org. Khim.,50, 1037 (1980).Google Scholar
  10. 10.
    W. T. Ford and J. B. Grutzner, J. Org. Chem.,37, 2561 (1972).Google Scholar
  11. 11.
    U. M. Dzhemilev, A. G. Ibragimov, E. V. Gribanova, and L. M. Khalilov, Izv. Akad. Nauk SSSR, Ser. Khim., 2566 (1985).Google Scholar
  12. 12.
    J. Quere and E. Marechal, Bull. Soc. Chim. France, 4087 (1969).Google Scholar
  13. 13.
    W. Wislicenus and W. Mocker, Chem. Ber.,46, 2772 (1913).Google Scholar
  14. 14.
    A. C. Cope and F. A. Hochstein, J. Am. Chem. Soc.,72, 2515 (1950).Google Scholar
  15. 15.
    V. D. Azatyan, Dokl. Akad. Nauk SSSR,48, 403 (1954).Google Scholar
  16. 16.
    H. Lemkuhl, S. Kintopf, and K. Mehler, J. Organomet. Chem.,46, Cl (1972).Google Scholar
  17. 17.
    H. J. Kablitz and G. Wilke, J. Organomet. Chem.,51, 241 (1973).Google Scholar

Copyright information

© Plenum Publishing Corporation 1988

Authors and Affiliations

  • U. M. Dzhemilev
    • 1
  • A. G. Ibragimov
    • 1
  • E. V. Gribanova
    • 1
  • L. M. Khalilov
    • 1
  1. 1.Institute of Chemistry, Bashkir BranchAcademy of Sciences of the USSRUfa

Personalised recommendations