Photogeneration of o-Quinone Methides from o-Cycloalkenylphenols

Journal of Organic Chemistry

Volumn 68, Issue 25, 2003, Pages 9643-9647

  Leo, Edgar A ^a   Delgado, Julio ^a   Domingo, Luis R ^b   Espinós, Amparo ^a   Miranda, Miguel A ^a   Tormos, Rosa ^a  

^a UNIVERSITAT POLITÈCNICA DE VALÈNCIA   (Spain)

^b UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; METHANOL; PHENOLS; PHOTOLYSIS; PROBABILITY DENSITY FUNCTION;

PHOTOGENERATION;

KETONES;

2 CYCLOHEXENONE DERIVATIVE; 2 QUINONE METHIDE DERIVATIVE; CYCLOHEXA 2,4 DIENONE DERIVATIVE; CYCLOHEXANONE DERIVATIVE; CYCLOPENTENE DERIVATIVE; METHANOL; PHENOL DERIVATIVE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION KINETICS; ELECTRON TRANSPORT; MOLECULAR MECHANICS; PHOTOACTIVATION; PHOTOGENERATION; PHOTOLYSIS; PROTON TRANSPORT; QUANTUM CHEMISTRY; REACTION ANALYSIS;

EID: 0345097545     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034918v     Document Type: Article

References (36)

1. Wan, P.; Barker, B.; Diao, L.; Fischer, M.; Shi, Y.; Yang, C. Can. J. Chem. 1996, 74, 465-475.
2. (a) Peter, M. G. Angew. Chem., Int. Ed. Engl. 1989, 101, 753-757.
3. (b) Bolton, J. L.; Pisha, E.; Zhang, F.; Qiu, S. Chem. Res. Toxicol. 1998, 11, 1113-1127.
4. (c) Pande, P.; Shearer, J.; Yang, J.; Greenber, W. A.; Rokita, S. E. J. Am. Chem. Soc. 1999, 121, 6773-6779.
5. (a) Foster, K. L.; Baker, S.; Brousmiche, D. W.; Wan, P. J. Photochem. Photobiol., A 1999, 129, 157-163.
6. (b) Barker, B.; Diao, L.; Wan, P. J. Photochem. Photobiol., A 1997, 104, 91-96.
7. (a) Chiang, Y.; Kresge, A. J.; Zhu, Y. J. Am. Chem. Soc. 2002, 124, 717-722.
8. (b) Chiang, Y.; Kresge, A. J.; Zhu, Y. Photochem. Photobiol. Sci. 2002, 1, 67-70.
9. (c) Chiang, Y.; Kresge, A. J.; Zhu, Y. J. Am. Chem. Soc. 2001, 123, 8089-8094.
10. (d) Chiang, Y.; Kresge, A. J.; Zhu, Y. J. Am. Chem. Soc. 2000, 122, 9854-9855.
11. (a) Brousmiche, D. W.; Wan, P. J. Photochem. Photobiol., A 2002, 149, 71-81.
12. (b) Diao, L.; Yang, C.; Wan, P. J. Am. Chem. Soc. 1995, 117, 5369-5370.
13. Fráter, G.; Schmid, H. Helv. Chim. Acta 1967, 50, 255-262.
14. Horspool, W. M.; Pauson, P. L. J. Chem. Soc., Chem. Commun. 1967, 22, 196-197.
15. (a) Shani, A.; Mechoulam, R. Tetrahedron 1971, 27, 601-606.
16. (b) Chow, Y. L.; Zhou, X. M.; Gaitan, T. J.; Wu, Z. Z. J. Am. Chem. Soc, 1989, 111, 3813-3818.
17. (a) Miranda, M. A.; Tormos, R. J. Org. Chem. 1993, 58, 3304-3307.
18. (b) Bosch-Montalvá, M. T.; Domingo, L. R.; Jiménez, M. C.; Miranda, M. A.; Tormos, R. J. Chem. Soc., Perkin Trans. 2 1998, 2175-2180.
19. Delgado, J.; Espinós, A.; Jiménez, M. C.; Miranda, M. A. Chem. Commun. 2002, 2636-2637.
20. Tarbell, D. S. The Claisen rearrangement. In Organic Reactions; Adams, R., Ed.; Wiley: New York, 1944; Vol. 2, pp 1-48.
21. Cristol, S. J.; Ilenda, C. S. J. Am. Chem. Soc. 1975, 97, 5862-5867.
22. Hosokawa, T.; Miyagi, S.; Murahashi, S.; Sonoda, A.; Matsuura, Y.; Tanimoto, S.; Kakudo, M. J. Org. Chem. 1978, 43, 719-724.
23. Murov, S. L.; Carmichael, I.; Hug, G. L. Handbook of Photochemistry, 2nd ed.; Marcel Dekker: New York, 1993; p 4.
24. Wehry, E. L.; Rogers, L. B. J. Am. Chem. Soc. 1965, 87, 4234-4238.
25. Marciniak, B.; Kozubek, H.; Paszyc, S. J. Chem. Educ. 1992, 69, 247-249.
26. Förster, T. Z. Elektrochem. 1950, 54, 521-535.
27. Liotta, C. L.; Smith, D. F.; Hopkins, H. P.; Rhodes, K. A. J. Phys. Chem. 1972, 76, 1909-1912.
28. (a) Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
29. (b) Ziegler, T. Chem. Rev. 1991, 91, 651-667.
30. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
31. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
32. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
33. (a) Schlegel, H. B. J. Comput. Chem. 1982, 3, 214-218.
34. (b) Schlegel, H. B. Geometry Optimization on Potential Energy Surfaces, In Modern Electronic Structure Theory; Yarkony, D. R., Ed.; World Scientific Publishing: Singapore, 1994.
35. Foresman, J. B.; Head-Gordon, M.; Pople, J. A.; Frisch, M. J. J. Phys. Chem. 1992, 96, 135-149.
36. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.6; Gaussian, Inc.: Pittsburgh, PA, 1998.