Chemistry of Heterocyclic Compounds

, Volume 26, Issue 8, pp 852–857 | Cite as

Photochemical reactions of 7-aminocoumarins. 5. [2+2]-Cycloadducts with trans-stilbene

  • M. A. Kirpichenok
  • D. S. Yufit
  • L. M. Mel'nikova
  • Yu. T. Struchkov
  • L. K. Denisov
  • I. I. Grandberg
Article
  • 41 Downloads

Abstract

The photocycloaddition of trans-stilbene to 7-diethylaminocoumarin, 4-methyl-7-diethylaminocoumarin, and 4-(N-morpholino)-7-diethylaminocoumarin was investigated. Adducts involving stereospecific (2+2)-cycloaddition at the 3–4 bond were isolated. On the basis of the PMR spectra and an x-ray diffraction study, it was established that the phenyl groups in the cycloadducts occupy 1-endo and 2-exo positions.

Keywords

Organic Chemistry Phenyl Adduct Diffraction Study Phenyl Group 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature Cited

  1. 1.
    M. A. Kirpichenok, L. M. Mel'nikova, L. K. Denisov, and I. I. Grandberg, Khim. Geterotsikl. Soedin., No. 4, 460 (1989).Google Scholar
  2. 2.
    M. A. Kirpichenok, L. M. Mel'nikova, D. S. Yufit, Yu. T. Struchkov, I. I. Grandberg, and L. K. Denisov, Khim. Geterotsikl. Soedin., No. 9, 1176 (1988).Google Scholar
  3. 3.
    G. Kaupp and E. Ringer, Tetrahedron Lett., 28, 6155 (1987).Google Scholar
  4. 4.
    F. D. Lewis, Advances in Photochemistry, D. M. Volman, S. Hammond, and K. Gollnick (eds.), Vol. 13, Wiley, New York (1986), p. 165.Google Scholar
  5. 5.
    G. Kaupp, M. Stark, and M. Fritz, Chem. Ber., 111, 3624 (1978).Google Scholar
  6. 6.
    P. P. Wells and H. Morrison, J. Am. Chem. Soc., 97, 154 (1975).Google Scholar
  7. 7.
    L. M. Tolbert and M. B. Ali, J. Am. Chem. Soc., 104, 1742 (1982).Google Scholar
  8. 8.
    O. Buchardt, J. J. Christensen, and N. Harrit, Acta Chem. Scand., B30, 189 (1976).Google Scholar
  9. 9.
    M. A. Kirpichenok, L. M. Mel'nikova, L. K. Denisov, and I. I. Grandberg, Khim. Geterotsikl. Soedin., No. 9, 1169 (1988).Google Scholar
  10. 10.
    G. O. Bekker, Introduction to the Photochemistry of Organic Compounds [in Russian], Khimiya, Leningrad (1976).Google Scholar
  11. 11.
    S. Parker, The Photoluminescence of Solutions [Russian translation], Mir, Moscow (1972).Google Scholar
  12. 12.
    R. G. Gerr, A. I. Yanovskii, and Yu. T. Struchkov, Kristallografiya, 12, 1029 (1983).Google Scholar

Copyright information

© Plenum Publishing Corporation 1991

Authors and Affiliations

  • M. A. Kirpichenok
    • 1
  • D. S. Yufit
    • 1
  • L. M. Mel'nikova
    • 1
  • Yu. T. Struchkov
    • 1
  • L. K. Denisov
    • 1
  • I. I. Grandberg
    • 1
  1. 1.K. A. Timiryazev Moscow Agricultural AcademyMoscow

Personalised recommendations