Phase-transfer-catalyzed preparation of spiro[2,4]-4,6-heptadienes by cycloalkylation of 1,3-cyclopentadiene with 1,2-dibromoalkanes

  • A. I. D'yachenko
  • L. G. Menchikov
  • O. M. Nefedov
Brief Communications


Cycloalkylation of cyclopentadiene with 1, 2-dibromo-n-alkanes with phase-transfer catalysis affords the spiro[2,4]-4,6-heptadienes in 70–85% yields. When the original 1, 2-dibromoalkanes contained one or two bromine atoms attached to tertiary carbon, none of the spiro[2,4]heptadienes were obtained.


Catalysis Bromine Spiro Bromine Atom Cyclopentadiene 
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.

Literature cited

  1. 1.
    M. J. Goldstein and R. Hoffmann, J. Am. Chem. Soc.,93, 6193 (1971).Google Scholar
  2. 2.
    P. E. Eilbracht and W. Totzauer, Chem. Ber.,115, 1669 (1982).Google Scholar
  3. 3.
    R. Ya. Levina, N. N. Mezentsova, and O. V. Lebedev, Zh. Org. Khim.,25, 1097 (1955).Google Scholar
  4. 4.
    C. F. Wilcox and R. R. Craig, J. Am. Chem. Soc.,83, 3866 (1961).Google Scholar
  5. 5.
    S. W. Staley and J. J. Rocchio, J. Am. Chem. Soc.91, 1565 (1969).Google Scholar
  6. 6.
    F. Meyer, P. Haynes, S. McLean, and A. G. Harrison, Can. J. Chem.,43, 211 (1965).Google Scholar
  7. 7.
    N. S. Zefirov, T. S. Kuznetsova, S. I. Kozhushkov, L. S. Surmina, and Z. A. Rashchupkina, Zh. Org. Khim.,19, 541 (1983).Google Scholar
  8. 8.
    M. Makosza, Polish Patent No. 55571 (1968); Chem. Abstr.,70, 106047f (1969).Google Scholar
  9. 9.
    H. Dürr, K. -H. Albert, and M. Kausch, Tetrahedron,35, 1285 (1979).Google Scholar
  10. 10.
    V. Veber and G. Gokel, Phase-Transfer Catalysis in Organic Chemistry [Russian translation], Mir, Moscow (1980).Google Scholar
  11. 11.
    E. V. Dehmlow and S. S. Dehmlow, Phase Transfer Catalysis, Verlag Chemie, (1980), pp. 101–133.Google Scholar
  12. 12.
    K. Weigand, Experimental Methods in Organic Chemistry [Russian translation], part 2, IL, Moscow (1952), p. 536.Google Scholar
  13. 13.
    G. A. Russell and H. C. Brown, J. Am. Chem, Soc.,77, 4029 (1955).Google Scholar

Copyright information

© Plenum Publishing Corporation 1985

Authors and Affiliations

  • A. I. D'yachenko
    • 1
  • L. G. Menchikov
    • 1
  • O. M. Nefedov
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow

Personalised recommendations