Photochemical cleavage and release of para-substituted phenols from α-keto amides

Journal of Organic Chemistry

Volumn 71, Issue 11, 2006, Pages 4206-4215

  Ma, Chicheng ^a   Chen, Yugang ^a   Steinmetz, Mark G ^a  

^a Marquette University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LASER FLASH PHOTOLYSIS; PARA ELECTRON RELEASING GROUPS; PHOTOCHEMICAL CLEAVAGES; PHOTOELIMINATION DECREASES;

HYDROGEN; IONS; KETONES; LASERS; NITROGEN COMPOUNDS; PHOTOLYSIS; QUANTUM THEORY;

PHENOLS;

5 METHYLENEOXAZOLIDIN 4 ONE; ALPHA KETO AMIDE DERIVATIVE; AMIDE; AMPHOLYTE; OXAZOLIDINE DERIVATIVE; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ELECTRON TRANSPORT; PHOTOACTIVATION; PHOTOLYSIS; PROTON TRANSPORT; QUANTUM YIELD; STRUCTURE ANALYSIS;

AMIDES; MOLECULAR STRUCTURE; PHENOLS; PHOTOCHEMISTRY;

EID: 33646913809     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060338x     Document Type: Article

References (42)

1. (a) Marriott, G., Ed. Methods in Enzymology; Academic Press: San Diego, CA, 1998.
2. (b) Givens, R. S.; Weber, J. F. W.; Conrad, P. G., II; Orosz, G.; Donahue, S. L.; Thayer, S. A. J. Am. Chem. Soc. 2000, 122, 2687-2697.
3. (c) Barth, A.; Corrie, J. E. T. Biophys. J. 2002, 83, 2864-2871.
4. (d) Kaplan, J. H.; Forbush, B., III; Hoffman, J. F. Biochemistry 1978, 17, 1929-1935.
5. (e) Canepari, M.; Nelson, L.; Papageorgiou, G.; Corrie, J. E. T.; Ogden, D. J. Neurosci. Methods 2001, 112, 29-42.
6. (a) Greenberg, M. M.; Venkatesan, H. J. Org. Chem. 1996, 61, 525-529.
7. (b) Greenberg, M. M.; Gilmore, J. L. J. Org. Chem. 1994, 59, 746-753.
8. (c) Pirrung, M. C.; Bradley, J.-C. J. Org. Chem. 1995, 60, 6270-6276.
9. (d) McGall, G. H.; Barone, A. D.; Diggelmann, M.; Fodor, S. P. A.; Gentalen, E.; Ngo, N. J. Am. Chem. Soc. 1997, 119, 5081-5090.
10. (e) Pease, A. C.; Solas, D.; Sullivan, E. J.; Cronin, M. T.; Holmes, C. P.; Fodor, S. P. A. Proc. Nat. Acad. Sci. U.S.A. 1994, 91, 5022-5026.
11. (f) Fodor, S. P. A.; Read, J. L.; Pirrung, M. C.; Stryer, L.; Lu, A. T.; Solas, D. Science 1991, 251, 767-773.
12. (g) Amit, B.; Hazum, E.; Fridkin, M.; Patchornik, A. Int. J. Peptide Protein Res. 1977, 9, 91-96.
13. (h) Lloyd-Williams, P.; Albericio, F.; Giralt, E. Tetrahedron 1993, 49, 11065-11133.
14. (a) Il'ichev, Y. V.; Schworer, M. A.; Wirz, J. J. Am. Chem. Soc. 2004, 126, 4581-4595.
15. (b) Walker, J. W.; Reid, G. P.; McCray, J. A.; Trentham, D. R. J. Am. Chem. Soc. 1988, 110, 7170-7177.
16. Park, C.-H.; Givens, R. S. J. Am. Chem. Soc. 1997, 119, 2453-2463.
17. Rajesh, C. S.; Givens, R. S.; Wirz, J. J. Am. Chem. Soc. 2000, 122, 611-618.
18. (a) Morrison, J.; Wan, P.; Corrie, J. E. T.; Papageorgiou, G. Photochem. Photobiol. Sci. 2002, 1, 960-969.
19. (a) Aoyama, H.; Sakamoto, M.; Kuwabara, K.; Yoshida, K.; Omote, Y. J. Am. Chem. Soc. 1983, 105, 1958-1964.
20. (b) Aoyama, H.; Sakamoto, M.; Omote, Y. J. Chem. Soc., Perkin Trans. 1 1981, 1357-1359.
21. (c) Aoyama, H.; Hasegawa, T.; Omote, Y. J. Am. Chem. Soc. 1979, 101, 5343-5347.
22. (d) Aoyama, H.; Hasegawa, T.; Watabe, M.; Shiraishi, H.; Omote, Y. J. Org. Chem. 1978, 43, 419-422.
23. Chesta, C. A.; Whitten, D. G. J. Am. Chem. Soc. 1992, 114, 2188-2197.
24. Wang R.; Chen C.; Duesler E.; Mariano P. S.; Yoon, U. C. J. Org. Chem. 2004, 69, 1215-1220.
25. (a) Ma, C.; Steinmetz, M. G.; Kopatz, E. J.; Rathore, R. J. Org. Chem. 2005, 70, 4431-4442.
26. (b) Ma, C.; Steinmetz, M. G.; Kopatz, E. J.; Rathore, R. Tetrahedron Lett. 2005, 46, 1045-1048.
27. (c) Ma, C.; Steinmetz, M. G.; Cheng, Q.; Jayaraman, V. Org. Lett. 2003, 5, 71-74.
28. Ma, C.; Steinmetz, M. G. Org. Lett. 2004, 6, 629-32.
29. Koft, E. R.; Dorf, P.; Kullnig, R. J. Org. Chem. 1989, 54, 2936-40.
30. Frimer, A. A.; Marks, V.; Gilinsky-Sharon, P.; Aljadeff, L.; Gottlieb, H. E. J. Org. Chem. 1995, 60, 4510-20.
31. Krishnamachari, V.; Levine, L. H.; Paré, P. W. J. Agric. Food Chem. 2002, 50, 4357-63.
32. (a) Netto-Ferreira, J. C.; Avellar, I. G. J.; Scaiano, J. C. J. Org. Chem. 1990, 55, 89-92.
33. (b) Palm, W.-U.; Dreeskamp, H.; Bouas-Laurent, H.; Castellan, A. Ber. Bunsen-Ges. Phys. Chem. 1992, 96, 50-61.
34. Grimme, S.; Dreeskamp, H. J. Photochem. Photobiol., A. 1992, 65, 371-382.
35. (a) Pratt, D. A.; de Heer, M. I.; Mulder, P.; Ingold, K. U. J. Am. Chem. Soc. 2001, 123, 5518-5526.
36. (b) Suryan, M. M.; Kafafi, S. A.; Stein, S. E. J. Am. Chem. Soc. 1989, 111, 4594-4600.
37. (a) Dileesh, S.; Gopidas, K. R. J. Photochem., Photobiol., A 2004, 162, 115-120.
38. (b) Rathore, R.; Kochi, J. K. Adv. Phys. Org. Chem. 2000, 35, 193-317.
39. Larson, Donald B.; Arnett, J. F.; Seliskar, C. J.; McGlynn, S. P. J. Am. Chem. Soc. 1974, 96, 3370-3380.
40. Hayes, N. V.; Branch, G. E. K. J. Am. Chem. Soc. 1943, 65, 1555-1564.
41. Mansch, C.; Muir, R. M.; Fujita, T.; Maloney, P. P.; Geiger, F.; Streich, M. J. Am. Chem. Soc. 1963, 85, 2817-2824.
42. Benington, F.; Morin, R. D. J. Org. Chem. 1961, 26, 194-197.