Photochemical transformations of polyfluoro-substituted stilbenes

  • N. I. Danilenko
  • M. I. Podgornaya
  • T. N. Gerasimova
  • E. P. Fokin
Organic Chemistry

Conclusions

  1. 1.

    When their dilute solutions in organic solvents are irradiated with UV light, polyfluoro-substituted trans-stilbene undergo, in the same way as the nonfluorinated analog, a transformation into the cis-isomer, but not photocyclization.

     
  2. 2.

    Irradiation of a concentrated solution of trans-2,3,4,5,6-pentafluorostilbene in a hydrocarbon solvent with visible or UV light leads to its partial dimerization into the derivatives of cyclobutane. In contrast to the nonfluorinated analog, pentafluorostilbene undergoes photodimerization in the solid phase.

     

Keywords

Hydrocarbon Organic Solvent Concentrate Solution Stilbene Cyclobutane 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    E. P. Fokin, T. N. Gerasimova, T. V. Fomenko, and N. V. Semikolenova, Zh. Org. Khim.,14, 835 (1978).Google Scholar
  2. 2.
    N. I. Danilenko, T. V. Fomenko, I. K. Korobeinicheva, T. N. Gerasimova, and E. P. Fokin, Izv. Akad. Nauk SSSR, Ser. Khim., 1606 (1980).Google Scholar
  3. 3.
    E. V. Blackburn and C. J. Timmons, Quart. Rev.,23, 482 (1969); E. N. Marvell, J. K. Reed, W. Gangler, and H. Tong, J. Org. Chem.,42, 3783 (1977); S. M. Kupchan and H. C. Wormer, Tetrahedron Lett., 359 (1965); R. Giles and M. Sargent, J. Chem. Soc. Perkin Trans.,1, 2447 (1974).Google Scholar
  4. 4.
    E. V. Aroskar, P. J. Brown, R. G. Plevey, and R. Stephens, J. Chem. Soc., 1569 (1968C).Google Scholar
  5. 5.
    A. Johnson, The Chemistry of Ylides [Russian translation], Mir, Moscow (1969), p. 185.Google Scholar
  6. 6.
    A. Gordon and R. Ford, Chemist's Guide [Russian translation], Mir, Moscow (1976), p. 302.Google Scholar
  7. 7.
    R. N. Beale and E. M. F. Roe, J. Chem. Soc., 2755 (1953).Google Scholar
  8. 8.
    J. Saltiel, J. Am. Chem. Soc.,90, 6394 (1968).Google Scholar
  9. 9.
    H. Shechter, W. J. Link, and G. V. D. Tieks, J. Am. Chem. Soc.,85, 1601 (1963).Google Scholar
  10. 10.
    H. Stegemejer, Chimia,19, 536 (1965).Google Scholar
  11. 11.
    M. L. Cross and C. L. Wilkins, Tetrahedron Lett., 3875 (1969).Google Scholar
  12. 12.
    E. Guggenheim and J. Prue, Physicochemical Calculations [Russian translation], IL (1958), p. 100.Google Scholar
  13. 13.
    L. N. Gribov and E. M. Popov, Dokl. Akad. Nauk SSSR,145, 761 (1962).Google Scholar
  14. 14.
    J. D. Dunitz, Acta Crystallogr.,2, 1 (1949).Google Scholar
  15. 15.
    M. Grayson and P. T. Keough, J. Am. Chem. Soc.,82, 3919 (1960).Google Scholar
  16. 16.
    I. L. Knunyants (editor), Syntheses of Fluoroorganic Compounds [in Russian], Khimiya, Moscow (1977), p. 162.Google Scholar
  17. 17.
    V. P. Molosnova, V. I. Vysochin, V. A. Barkhash, and N. N. Vorozhtsov, Jr., Izv. Akad. Nauk SSSR, Ser. Khim., 146 (1969).Google Scholar

Copyright information

© Plenum Publishing Corporation 1982

Authors and Affiliations

  • N. I. Danilenko
    • 1
  • M. I. Podgornaya
    • 1
  • T. N. Gerasimova
    • 1
  • E. P. Fokin
    • 1
  1. 1.Novosibirsk Institute of Organic ChemistrySiberian Branch of the Academy of Sciences of the USSRUSSR

Personalised recommendations