Photochemistry of 1,1 -bi-2-naphthol (BINOL) -ESIPT is responsible for photoracemization and photocyclization

Canadian Journal of Chemistry

Volumn 86, Issue 2, 2008, Pages 161-169

  Flegel, Mitchel ^a   Lukeman, Matthew ^a   Wan, Peter ^a  

^a UNIVERSITY OF VICTORIA   (Canada)

Author keywords

BINOL; ESIPT; Photocyclization; Photoprotonation; Photoracemization; Quinone methide

Indexed keywords

DEUTERIUM COMPOUNDS; IRRADIATION; PHOTOLYSIS; PROTON TRANSFER; SOLUTIONS;

BINOL; ESIPT; PHOTOCYCLIZATION; PHOTOPROTONATION; PHOTORACEMIZATION; QUINONE METHIDE;

ALCOHOLS;

EID: 39449090929     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/V07-143     Document Type: Article

References (34)

1. (a) S.M. Ormson and R.G. Brown. Prog. React. Kinet. 19, 45 (1994);
2. (b) D. Le Gourrierec, S. M. Ormson, and R.G. Brown. Prog. React. Kinet. 19, 211 (1994);
3. (c) S.J. Formosinho and L.G. Arnaut. J. Photochem. Photobiol. A, 75, 21 (1993).
4. Representative papers: (a) P-T. Chou, J.-H. Liao, C.-Y Wei, C.-Y Yang, W.-S. Yu, and Y.-H. Chou. J. Am. Chem. Soc. 112, 986 (2000);
5. (b) A. Kyrychenko, J. Herbich, M. Izydorzak, F. Wu, R. P. Thummel, and J. Waluk. J. Am. Chem. Soc. 112, 11179 (1999);
6. (c) W.-H. Fang. J. Am. Chem. Soc. 120, 7568 (1998);
7. (d) M.C. Rios Rodriguez, J.C. Penedo, R.J. Willemse, M. Mosquera, and F. Rodriguez-Prieto. J. Phys. Chem. A, 103, 7236 (1999);
8. (e) S. Ameer-Beg, S. M. Ormson, R.G. Brown, P. Matousek, M. Towrie, E.T. Nibbering, P. Foggi, and F.V.R. Neuwahl. J. Phys. Chem. A, 105, 3709 (2001);
9. (f) P.-T. Chou, Y.-C. Chen, W.-S. Yu, Y.-H. Chou, C.-Y. Wei, and Y.-M. Cheng. J. Phys. Chem. A, 105, 1731 (2001);
10. (g) M. Fischer and P. Wan. J. Am. Chem. Soc. 121, 4555 (1999);
11. (h) M. Fischer and P. Wan. J. Am. Chem. Soc. 120, 2680 (1998).
12. (a) M. Lukeman and P. Wan. J. Am. Chem. Soc. 124, 9458 (2002);
13. (b) M. Lukeman and P. Wan. J. Am. Chem. Soc. 125, 1164 (2003).
14. (a) J. M. Brunel. Chem. Rev. 105, 857 (2005);
15. (b) L. Pu. Chem. Rev. 104, 1687 (2004).
16. M. Cavazza, M. Zandomeneghi, A. Ouchi, and Y. Koga. J. Am. Chem. Soc. 118, 9990 (1996).
17. T. Hattori, Y Shimazumi, O. Yamabe, E. Koshiishi, and S. Miyano. Chem. Commun. (Cambridge), 2234 (2002).
18. Representative papers: (a) N. B. Barhate and C.-T. Chen. Org. Lett. 4, 2529 (2002);
19. (b) S. Herres, P. Hesemann, and J.J.E. Moreau. Eur. J. Org. Chem. 99 (2003);
20. (c) M.-H. Xu, J. Lin, Q.-S. Hu, and L. Pu. J. Am. Chem. Soc. 124, 14239 (2002).
21. (a) R.A. Moore, J. Lee, and G. W. Robinson. J. Phys. Chem. 89, 3648 (1985);
22. (b) J. Lee, G.W. Robinson, S.P. Webb, L.A. Philips, and J.H. Clark. J. Am. Chem. Soc. 108, 6538 (1986);
23. (c) G.W. Robinson. J. Phys. Chem. 95, 10386 (1991);
24. (d) L.M. Tolbert and J.E. Haubrich. J. Am. Chem. Soc. 116, 10593 (1994).
25. D. Budac and P. Wan. J. Org. Chem, 57, 887 (1992).
26. (a) K.S. Bumham and G.B. Schuster. J. Am, Chem. Soc. 120, 12619 (1998);
27. (b) M. Irie, K. Yoshida, and K. Hayashi. J. Phys. Chem. 81, 969 (1977);
28. (c) H.E. Zimmerman and D.S. Crumrine. J. Am. Chem. Soc. 94, 498 (1972).
29. L. Meca, D. Reha, and Z. Havias. J. Org. Chem. 68, 5677 (2003).
30. S. Fujiyoshi, S. Takeuchi, and T. Tahara. J. Phys. Chem. A, 108, 5938 (2004).
31. M. Flegel, M. Lukeman, L.A. Huck, and P. Wan. J. Am. Chem. Soc. 126, 7890 (2004).
32. F. Toda, K. Tanaka, H. Miyamoto, H. Koshima, I. Miyahara, and K. Hirotsu. J. Chem. Soc. Perkin Trans. 2, 1877 (1997).
33. L. Diao, C. Yang, and P. Wan. J. Am. Chem. Soc. 117, 5369 (1995).
34. Y. Shi and P. Wan. Can. J. Chem. 83, 1306 (2005).