Advertisement

Photochemical [2+2]-cycloaddition of α,β-unsaturated ketones to acetylene substrates and phototransformation of the adducts

  • É. P. Serebryakov
Organic Chemistry

Keywords

Adduct Ketone Acetylene Acetylene Substrate 
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.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    P. G. Bauslaugh, Synthesis, 287 (1970).Google Scholar
  2. 2.
    P. deMayo, Accounts Chem. Res.,4, 41 (1971).Google Scholar
  3. 3.
    S. W. Baldwin, Org. Photochemistry,5, 123 (1981).Google Scholar
  4. 4.
    G. R. Lenz, Rev. Chem. Interned.,4, 369 (1980).Google Scholar
  5. 5.
    E. J. Corey, J. D. Bass, R. LeMahieu, and R. B. Mitra, J. Am. Chem. Soc.,86, 5570 (1964).Google Scholar
  6. 6.
    K. Wiesner, Tetrahedron,31, 1653 (1975).Google Scholar
  7. 7.
    R. Criegee and H. Furrer, Chem. Ber.,97, 2949 (1964).Google Scholar
  8. 8.
    P. E. Eaton, Tetrahedron Lett., 2695 (1964).Google Scholar
  9. 9.
    R. L. Cargill, M. E. Bekcham, A. Siebert, and J. Dorn, J. Org. Chem.,30, 3647 (1965).Google Scholar
  10. 10.
    P. Sunder-Plassman, P. H. Nelson, P. H. Boyle, A. Cruz, J. Iriarte, P. Crabe, J. A. Zderić, J. A. Edwards, and J. H. Fried, J. Org. Chem.,34, 3779 (1969).Google Scholar
  11. 11.
    J. W. Hanifin and E. J. Cohen, J. Am. Chem. Soc.,91, 4494 (1969).Google Scholar
  12. 12.
    R. L. Cargill and J. W. Crawford, J. Org. Chem.,35, 356 (1970).Google Scholar
  13. 13.
    W. S. Agosta and W. W. Lowrance, J. Org. Chem.,35, 3851 (1970).Google Scholar
  14. 14.
    D. S. Owsley and J. J. Bloomfield, J. Chem. Soc. (C), 3445 (1971).Google Scholar
  15. 15.
    P. deMayo and M. C. Usselman, An. Quim. Real Soc. Esp. Fis. Quim.,68, 779 (1972).Google Scholar
  16. 16.
    T. Swensson, Chem. Scr.,3, 171 (1973).Google Scholar
  17. 17.
    S. D. Kulomzina, E. P. Serebryakov, and V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim., 2055 (1974).Google Scholar
  18. 18.
    S. D. Kulomzina, É. P. Serebryakov, and V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim., 855 (1977).Google Scholar
  19. 19.
    A. Kh. Margaryan, É. P. Serebryakov, and V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim., 418 (1977).Google Scholar
  20. 20.
    A. Kh. Margaryan, É. P. Serebryakov, and V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim., 408 (1978).Google Scholar
  21. 21.
    É. P. Serebryakov, S. D. Kulomzina, A. Kh. Margaryan, and O. S. Chizhov, Izv. Akad. Nauk SSSR, Ser. Khim., 1798 (1977).Google Scholar
  22. 22.
    É. P. Serebryakov, L. M. Kostochka, and V. F. Kucherov, Zh, Org. Khim.,9, 2375 (1973).Google Scholar
  23. 23.
    M. I. Struchkova, A. Kh. Margaryan, and É. P. Serebryakov, Izv. Akad. Nauk SSSR, Ser. Khim., 56 (1980).Google Scholar
  24. 24.
    A. Kh. Margaryan, É. P. Serebryakov, and V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim., 840 (1967).Google Scholar
  25. 25.
    J. J. McCullough, B. R. Ramachandran, F. F. Snyder, and G. N. Taylor, J. Am. Chem. Soc.,97, 6767 (1975).Google Scholar
  26. 26.
    R. O. Loutfy and P. deMayo, J. Am. Chem. Soc.,99, 3559 (1977).Google Scholar
  27. 27.
    É. P. Serebryakov, A. Kh. Margaryan, and V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim., 416 (1978).Google Scholar
  28. 28.
    É. P. Serebryakov, S. D. Kulomzina-Pletneva, and A. Kh. Margaryan, Tetrahedron,15, 77 (1979).Google Scholar
  29. 29.
    É. P. Serebryakov, S. D. Kulomzina, and V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim., 862 (1977).Google Scholar
  30. 30.
    É. P. Serebryakov, S. D. Kulomzina, and V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim., 2739 (1975).Google Scholar
  31. 31.
    R. L. Cargill, W. A. Bundy, D. M. Pond, A. B. Sears, J. Saltiel, and J. Winterle, Mol. Photochem.,3, 123 (1971).Google Scholar
  32. 32.
    G. Marsch, D. R. Kearns, and K. Schaffner, J. Am. Chem. Soc.,93, 3129 (1971).Google Scholar
  33. 33.
    K. Ya. Burstein and É. P. Serebryakov, Tetrahedron,34, 3233 (1978).Google Scholar
  34. 34.
    O. A. Osipov, V. I. Minkin, and A. D. Garnovskii, Handbook of Dipole Moments [in Russian], Vysshaya Shkola, Moscow (1979).Google Scholar
  35. 35.
    W. Herz and M. G. Nair, J. Am. Chem. Soc.,89, 547 (1967).Google Scholar
  36. 36.
    R. L. Cargill, T. Y. King, A. B. Sears, and M. R. Wilcott, J. Org. Chem.,36, 1423 (1971).Google Scholar
  37. 37.
    A. V. Kamernitskii, V. N. Ignatov, I. S. Levina, É. P. Serebryakov, G. V. Nikitina, and V. V. Korkhov, Khim.-Farm. Zh.,11, No. 10, 96 (1977).Google Scholar
  38. 38.
    É. P. Serebryakov, V. F. Kucherov, and G. Adam, Izv. Akad. Nauk SSSR, Ser. Khim., 1831 (1977).Google Scholar
  39. 39.
    B. Voigt and G. Adam, Tetrahedron,32, 1581 (1976).Google Scholar
  40. 40.
    É. P. Serebryakov, Izv. Akad. Nauk SSSR, Ser. Khim., 2313 (1979).Google Scholar
  41. 41.
    P. Sunder-Plassman, J. Zderic, and J. H. Fried, Tetrahedron Lett., 3451 (1966).Google Scholar
  42. 42.
    M. Rubin, T. Maymon, and D. Glover, Isr. J. Chem.,8, 717 (1970).Google Scholar
  43. 43.
    G. R. Lenz, Tetrahedron,28, 2195 (1972).Google Scholar
  44. 44.
    É. P. Serebryakov and I. M. Vol'pin, Izv. Akad. Nauk SSSR, Ser. Khim., 123 (1983).Google Scholar
  45. 45.
    É. P. Serebryakov, L. G. Vorontsova, O. S. Chizhov, V. A. Pavlov, and I. M. Vol'pin, Izv. Akad. Nauk SSSR, Ser. Khim., 132 (1983).Google Scholar
  46. 46.
    H. B. Henbest and W. B. Jackson, J. Chem. Soc., (C), 2459 (1967); ibid., 2465 (1967).Google Scholar
  47. 47.
    P. A. Kollman, D. D. Giannini, W. L. Duax, S. Rotenberg, and M. E. Wolf, J. Am. Chem. Soc.,95, 2869 (1973).PubMedGoogle Scholar
  48. 48.
    É. P. Serebryakov, S. D. Kulomzina, and V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim., 2760 (1977).Google Scholar
  49. 49.
    P. H. Boyle, W. Cocker, D. H. Grayson, and P. V. B. Shannon, J. Chem. Soc. (C), 1073 (1971).Google Scholar
  50. 50.
    É. P. Serebryakov, S. D. Kulomzina, and V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim., 1904 (1977); USSR Patent No. 639854, Byull. Izobret., No. 48 (1978).Google Scholar

Copyright information

© Plenum Publishing Corporation 1984

Authors and Affiliations

  • É. P. Serebryakov
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow

Personalised recommendations