Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Photodimerization of 5,7-Dimethoxycoumarin

  • Shim, Sang Chul (Department of Chemistry, The Korea Advanced Institute of Science and Technology) ;
  • Jeong, Bong Mo (Department of Chemistry, The Korea Advanced Institute of Science and Technology) ;
  • Paik Young Hee (Department of Chemistry, The Korea Advanced Institute of Science and Technology)
  • Published : 1992.12.20
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Abstract

Three photocyclodimers of 5,7-dimethoxycoumarin (DMC) were isolated and characterized from the photolysis of DMC in acetonitrile. The configuration of the dimers was found to be anti head-to-head, syn head-to-head and syn head-to-tail, respectively. The number and the ratio of the products are solvent dependent. The anti head-to-head dimer is favored in nonpolar solvents and the preference decreases as the solvent polarity increases giving almost 100${\%}$ syn dimers and less than 1${\%}$ anti dimer from methanol solution. The overall yields of dimers also increase with the solvent polarity. From sensitization and quenching experiments, anti dimer was found to be formed via excited singlet state while syn dimers were formed via both excited singlet and triplet states.

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References

  1. Photochem. Photobiol. v.24 C. N. Ou;P. S. Song;M. L. Harter;I. C. Felkner
  2. Photochem. Photobiol. v.24 M. L. Harter;I. C. Felkner;P. S. Song;
  3. J. Am. Chem. Soc. v.95 W. W. Mantulin;P. S. Song
  4. Biochem. v.17 C. N. Ou;C. H. Tsai;K. J. Tapley;P. S. Song
  5. Chem. Lett. S. C. Shim;D. Y. Chi
  6. Photochem. Photobiol. v.30 S. C. Shim;K. H. Chae;D. Y. Chi
  7. Photochem. Photobiol. v.34 S. C. Shim;H. Y. Koh;D. Y. Chi
  8. Photochem. Photobiol. v.46 S. C. Shim;H. K. Shim;T. H. Cho
  9. Chem. Lett. v.19 S. C. Shim;H. K. Shim;T. H. Cho
  10. Photochem. Photobiol. v.27 S. C. Shim;K. Y. Choi;P. S. Song
  11. Tetrahedron v.19 V. Georgian;L. Georgian;A. V. Roberts
  12. Chem. Ber. v.99 C. H. Krauch;S. Farid;G. O. Schenck
  13. Tetrahedron v.23 I. Fleming;D. H. Williams
  14. J. Org. Chem. v.35 L. Paolillo;H. Ziffer;O. Buchardt
  15. J. Am. Chem. Soc. v.93 M. Barfield
  16. J. Org. Chem. v.38 G. Montaudo;S.Caccamese
  17. J. Org. Chem. v.50 K. Gnanauguru;N. Ramasubbu;N. Venkatesar;V. Ramamurthy
  18. J. Chem. Phys. v.38 D. M. Grant;R. C. Hirst;H. S. Gutowsky
  19. J. Am. Chem. Soc. v.89 E. Lusting;E. P. Ragelis;N. Duy;J. A. Ferretti
  20. NMR Spectroscopy H. Gunther
  21. J. Org. Chem. v.38 L. H. Leenders;E. Schouteden;F. C. De Schryver
  22. Photochem. Photobiol. v.21 J. Gervais;F. C. De Schryver
  23. J. Am. Chem. Soc. v.86 D. Valentine;N. J. Turro;G. S. Hammond
  24. Organic Photochemistry v.2 A. Padwa
  25. J. Am. Chem. Soc. v.86 G. S. Hammond;C. A. Stout;A. A. Lamola
  26. Nouv. J. Chim. v.3 J. Gervais;N. Boens;F. C. De Schryver
  27. J. Am. Chem. Soc. v.89 N. Yang;R. Loeschen;D. Mitchell
  28. Tetrahedron Lett. v.14 D. O. Cowan;R. L. Drisco
  29. J. Am. Chem. Soc. v.88 H. Morrison;H. Curtis;T. McDowell

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