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Chemistry of Heterocyclic Compounds

, Volume 24, Issue 9, pp 965–974 | Cite as

Photochemical reactions of 7-aminocoumarins. 2. [2 + 2]-cycloadducts with styrene

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

Abstract

The photocycloaddition of styrene to 4-methyl-7-aminocoumarin, 4-methyl-7-diethylaminocoumarin, 7-(N-morpholino) coumarin, 3-ethoxycarbonylmethyl-4-methyl-7-diethylaminocoumarin, and coumarin-102 (2,3,6,7-tetrahydro-9-methyl-1H, 5H,11H-[l]-benzopyrano[6,7,8-ij] quinolizin-11-one) was investigated. Adducts of regio- and stereospecific [2 + 2]-cycloaddition to the 3–4 bond were isolated. It was established by means of x-ray diffraction analysis that the phenyl group in the cycloadducts occupies the 1-endo position. The participation of the singlet excited states of the 7-aminocoumarin molecules in [2 + 2]-cycloaddition was demonstrated.

Keywords

Organic Chemistry Phenyl Adduct Excited State Styrene 
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.

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Copyright information

© Plenum Publishing Corporation 1989

Authors and Affiliations

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

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