Chemistry of Heterocyclic Compounds

, Volume 16, Issue 3, pp 252–255 | Cite as

9-Alkenylcarbazoles. 6. Synthesis and structure of cis-9-propenylcarbazoles

  • V. D. Filimonov
  • S. G. Gorbachev
  • E. E. Sirotkina


A number of cis-9-propenylcarbazoles were synthesized in good yields by isomerization of 9-allylcarbazoles by the action of tert-BuOK in dimethyl sulfoxide. It was established that cis-9-propenylcarbazole is less thermodynamically stable than its trans isomer. It was shown by13C NMR, UV, and IR spectroscopy that the effect of p-π conjugation in cis-9-propenylcarbazole decreases as compared with the trans isomer as a result of the noncoplanarity of the C=C bond and the carbazole ring.


Spectroscopy Organic Chemistry Dimethyl Sulfoxide Dimethyl Sulfoxide 
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.
    V. D. Filimonov, V. A. Anfinogenov, and E. E. Sirotkina, Khim. Geterotsikl. Soedin., No. 4, 497 (1979).Google Scholar
  2. 2.
    V. D. Filimonov, V. A. Anfinogenov, and E. E. Sirotkina, Zh. Org. Khim.,14, 2607 (1978).Google Scholar
  3. 3.
    A. J. Hubert, J. Chem. Soc., C, No. 16, 2048 (1968).Google Scholar
  4. 4.
    M. Julia, A. Schouteeten, and M. Baillard, Tetrahedron Lett., No. 38, 3433 (1974).CrossRefGoogle Scholar
  5. 5.
    V. P. Lopatinskii, E. E. Sirotkina, and S. A. Bazdyreva, USSR Inventor's Certificate No. 193518 (1965); Byul. Izobr., No. 7, 38 (1967).Google Scholar
  6. 6.
    T. Sauer and H. Prahl, Ber.,102, 1917 (1969).Google Scholar
  7. 7.
    V. D. Filimonov, V. A. Anfinogenov, and N. E. Matyukov, Khim. Geterotsikl. Soedin., No. 10, 1368 (1976).Google Scholar
  8. 8.
    H. Henry and S. Fliszar, J. Am. Chem. Soc.,100, 3312 (1978).CrossRefGoogle Scholar
  9. 9.
    E. S. Stern and C. J. Timmons (eds.), Gillam and Stern's: Introduction to Electronic Absorption Spectroscopy in Organic Chemistry, 3rd ed., St. Martin (1971).Google Scholar
  10. 10.
    K. Tsutsui, K. Hisotsu, M. Umesaki, M. Kurahashi, A. Simada, and T. Higuchi, Acta Cryst.,B32, 3049 (1976).Google Scholar
  11. 11.
    H. Suzuki, Bull. Chem. Soc. Jpn.,33, 619 (1960).Google Scholar
  12. 12.
    B. A. Trofimov, N. I. Golovanova, A. I. Mikhaleva, S. E. Korostova, A. N. Vasil'ev, and L. N. Balabanova, Khim. Geterotsikl. Soedin., No. 7, 910 (1977).Google Scholar
  13. 13.
    T. Okuyama, T. Fueno, and J. Furukawa, Tetrahedron,25, 5409 (1969).CrossRefGoogle Scholar
  14. 14.
    E. Taskinen and P. Liukas, Acta Chem. Scand.,28B, 114 (1974).CrossRefGoogle Scholar
  15. 15.
    V. D. Filimonov, V. A. Anfinogenov, and E. E. Sirotkina, Zh. Org. Khim.,14, 2550 (1978).Google Scholar
  16. 16.
    S. G. Gorbachev, V. D. Filimonov, and E. E. Sirotkina, Vysokomol. Soedin.,21B, 125 (1979).Google Scholar

Copyright information

© Plenum Publishing Corporation 1980

Authors and Affiliations

  • V. D. Filimonov
    • 1
  • S. G. Gorbachev
    • 1
  • E. E. Sirotkina
    • 1
  1. 1.S. M. Kirov Tomsk Polytechnic InstituteTomsk

Personalised recommendations