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Lewis Acid Catalysis of Coumarin and 5,7-Dimethoxycoumarin Photodimerization

  • Shim, Sang-Chul (Department of Chemistry, Korea Advanced Institute of Science and Technology) ;
  • Kim, Eun-Il (Department of Chemistry, Korea Advanced Institute of Science and Technology) ;
  • Lee, Ki-Taek (Department of Chemistry, Korea Advanced Institute of Science and Technology)
  • Published : 1987.06.20

Abstract

The effect of Lewis acids on spectroscopic properties and photodimerization of coumarin and 5,7-dimethoxycoumarin was investigated. Quantum yields of coumarin photodimerization increase in the presence of $BF_3{\cdot}OEt_2$ but those of 5,7-dimethoxycoumarin decrease. The spectroscopic properties of the coumarin-$BF_3{\cdot}OEt_2$ and 5,7-dimethoxycoumarin-$BF_3{\cdot}OEt_2$ complexes were studied by UV, IR, $^1H$ NMR and fluorescence spectroscopy.

Keywords

References

  1. Frontier Orbitals and Organic Chemical Reactions I. Flemming
  2. J. Am. Chem. Soc. v.95 K.N. Houk;R.W. Strozier
  3. J. Am. Chem. Soc. v.103 F.D. Lewis;J.D. Oxman
  4. J. Am. Chem. Soc. v.108 F.D. Lewis;J.D. Oxman;L.L. Gibson;H.L. Hampsch;S.L. Quillen
  5. J. Am. Chem. Soc. v.108 F.D. Lewis;D.K. Howard;S.V. Barancyk;J.D. Oxman
  6. J. Am. Chem. Soc. v.108 F.D. Lewis;D.K. Howard;J.D. Oxman;A.L. Upthagrove;S.L. Quillen
  7. J. Chem. Soc., Chem. Commun N.W. Alcock;N. Herron;T.J. Kemp;C.N. Shoppe
  8. Ber. v.43 P. Praetorius;F. Korn
  9. J. Am. Chem. Soc. v.105 F.D. Lewis;D.K. Howard;J.D. Oxman
  10. J. Am. Chem. Soc. v.106 F.D. Lewis;J.D. Oxman
  11. Proc. Roy. Soc. (London) A v.235 C.G. Hatchard;C.A. Parker
  12. Photochem. Photobiol. v.27 S.C. Shim;K.Y. Choi;P.-S. Song
  13. Aust. J. Chem. v.22 R.C. Paul;S.L. Chadha
  14. Principles of Fluorescence Spectroscopy J.R. Lakowich
  15. J. Luminesc. v.12;13 P.-S. Song;Q. Chae

Cited by

  1. Photophysical and photochemical properties of 5,7-dimethoxycoumarin under one- and two-photon excitation vol.16, pp.1, 2003, https://doi.org/10.1002/poc.576
  2. Enantioselective Lewis Acid Catalysis in Intramolecular [2 + 2] Photocycloaddition Reactions: A Mechanistic Comparison between Representative Coumarin and Enone Substrates vol.137, pp.15, 1987, https://doi.org/10.1021/jacs.5b01740
  3. Brønsted‐Säure‐Katalyse der [2+2]‐Photocycloaddition von Enondithianen bei Bestrahlung mit sichtbarem Licht vol.129, pp.15, 1987, https://doi.org/10.1002/ange.201700837
  4. Brønsted Acid Catalysis in Visible‐Light‐Induced [2+2] Photocycloaddition Reactions of Enone Dithianes vol.56, pp.15, 2017, https://doi.org/10.1002/anie.201700837
  5. Chromophoraktivierung von α,β‐ungesättigten Carbonylverbindungen und ihre Anwendung in enantioselektiven Photoreaktionen vol.130, pp.44, 1987, https://doi.org/10.1002/ange.201804006
  6. Chromophore Activation of α,β‐Unsaturated Carbonyl Compounds and Its Application to Enantioselective Photochemical Reactions vol.57, pp.44, 1987, https://doi.org/10.1002/anie.201804006