DOI QR코드

DOI QR Code

Photoacid Catalyzed Reaction of Phenol with Styrene

  • Kim, Vicna (Department of Chemistry, Sunchon National University) ;
  • Shin, Eun Ju (Department of Chemistry, Sunchon National University) ;
  • Chung, Minchul (Department of Chemical Engineering, Sunchon National University) ;
  • Ahn, Hogeun (Department of Chemical Engineering, Sunchon National University) ;
  • Kwak, Wonbong (SFC. Co., Ltd.)
  • Received : 2015.12.30
  • Accepted : 2016.03.18
  • Published : 2016.06.30

Abstract

The reaction of styrene with phenol using photoacid catalyst has been investigated. Upon irradiation with 450 nm light, protonated merocyanine photoacid converts into spiropyran form with releasing proton. The reaction of styrene with phenol has been conducted under irradiation with 450 nm light using merocyanine photoacid catalyst at room temperature in comparison with the results using some selected catalysts including $H_2SO_4$ or $FeCl_3$ at the reaction temperature of $120^{\circ}C$.

Keywords

References

  1. Pritchard, G. Plastic Additives, An A_Z reference, Springer, England, 1998.
  2. Manedova, P. Sh.; Farzaliev, V. M.; Velieva, F. M.; Babaev, E. R. Petroleum Chemistry, 2007, 47, 55-60. https://doi.org/10.1134/S0965544107010070
  3. Weissermel, K.; Arpe, H. J. Industrielle Organische Chemie, 5th ed., Wiley-VCH, Weinheim, Germany, 1988, p. 167.
  4. Bandini, M.; Emer, E.; Tommasi, S.; Umani-Ronchi, A. Eur. J. Org. Chem., 2006, 3527-3544.
  5. Kischel, J.; Jovel, I.; Mertins, K.; Zapf, A.; Beller, M. A. Org. Lett., 2006, 8(1), 19-22.
  6. Mohan, D. C.; Patil, R. D.; Adimurthy, S. Eur. J. Org. Chem., 2012, 3520-3525.
  7. Shi, Z.; Peng, P.; Strohecker, D.; Liao, Y. J. Am. Chem. Soc. 2011, 133, 14699-14703. https://doi.org/10.1021/ja203851c
  8. Ramsey, S.; Mokrab, Y.; Carvacho, I.; Sands, Z. A.; Sansom, M. S. P.; Clapham, D. E. Nat. Struct. Mol. Biol. 2010, 17, 869-875. https://doi.org/10.1038/nsmb.1826
  9. Li, J.; Liu, Z.; Tan, C.; Guo, X.; Wang, L.; Sancar, A.; Zhong, D. Nature 2010, 466, 887-890. https://doi.org/10.1038/nature09192
  10. Tolbert, L.; Solntsev, K. M. Acc. Chem. Res. 2002, 35, 19-27. https://doi.org/10.1021/ar990109f
  11. Dempsey, J. L.; Winkler, J. R.; Gray, H. B. J.Am. Chem. Soc. 2010, 132, 16774-16776. https://doi.org/10.1021/ja109351h
  12. Morimoto, M.; Irie, M. Chem. Commun. 2011, 47, 4186-4188. https://doi.org/10.1039/c0cc05729k
  13. Nunes, R. M. D.; Pineiro, M.; Arnaut, L. G. J. Am. Chem. Soc. 2009, 131, 9456-9462. https://doi.org/10.1021/ja901930c
  14. Duerr, H.; Bouas-Laurent, H. Photochromism : Molecules and Systems, Revised Edition, Elsevier, Amsterdam, The Netherlands, 2003.
  15. Gil, M.; Ziolek, M.; Organero, J. A.; Douhal, A. J. Phys. Chem. C 2010, 114, 9554-9562.
  16. Silvi, S.; Arduini, A.; Pochini, A.; Secchi, A.; Tomasulo, M.; Raymo, F. M.; Baroncini, M.; Credi, A. J. Am. Chem. Soc. 2007, 129, 13378-13379. https://doi.org/10.1021/ja0753851
  17. Raymo, F. M.; Alvarado, R. J.; Giordani, S.; Cejas, M. A. J. Am. Chem. Soc. 2003, 125, 2361-2364. https://doi.org/10.1021/ja027977j
  18. Emond, M.; Sun, J.; Gregoire, J.; Maurin, S.; Tribet, C.; Jullien, L. Phys. Chem. Chem. Phys. 2011, 13, 6493-6499. https://doi.org/10.1039/c0cp02464c
  19. Nakashima, T.; Tsuchie, K.; Kanazawa, R.; Li, R.; Iijima, S.; Galangau, O.; Nakagawa, H.; Mutoh, K.; Kobayashi, Y.; Abe, J.; Kawai, T. J. Am. Chem. Soc. 2015, 137, 7023-7026. https://doi.org/10.1021/jacs.5b02826