Photoinduced radical cleavage of bromophenyl ketones

Journal of the American Chemical Society

Volumn 118, Issue 4, 1996, Pages 746-754

  Wagner, Peter J ^a   Sedon, James H ^a   Gudmundsdottir, Anna ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0010420922     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja952782f     Document Type: Article

References (68)

1. (a) Sharma, R. K.; Kharasch, N. Angew. Chem., Int. Ed. Engl. 1968, 7, 36.
2. (b) Pinhey, J T.; Rigby, R. D G. Tetrahedron Lett. 1969, 1267.
3. (c) Fox, M., Nichols, W. C., Lemal, D. M. J. Am. Chem. Soc 1973, 95, 8164.
4. 3
5. Barltrop, J. A.; Coyle, J. D. Excited States in Organic Chemistry; Wiley: London, 1975.
6. Nagaoka, S.; Takemura, T., Baba, H. Bull. Chem. Soc. Jpn. 1985, 58, 2082.
7. Dzvornik, M., Yang, S.; Bersohn, R. J. Chem. Phys. 1974, 61, 4408.
8. Hwang, H. J.; El-Sayed, M. A. J. Chem. Phys. 1992, 96, 856.
9. Nakaoka, S.; Takemura, T.; Baba, H., Koga, N.; Morokuma, K. J. Phys Chem. 1986, 90, 759.
10. (a) Rentzepis, P.; Mitschele, C. J. Anal. Chem. 1970, 42, 20A.
11. (b) Anderson, R. W., Jr.; Hochstrasser, R. M.; Lutz, H.; Scott, G. W. Chem. Phys. Lett. 1974, 28, 153.
12. Wagner, P. J., Truman, R. J., Scaiano, J. C. J. Am. Chem. Soc. 1985, 107, 7093.
13. (a) Baum, E. J.; Pitts, J. N J. Phys. Chem. 1966, 70, 2066.
14. (b) Baum, E. J.; Wan, J. K. S.; Pins, J. N. J. Am. Chem. Soc. 1966, 88, 2652.
15. Wagner, P. J.; Waite, C. I. J. Phys. Chem. 1995, 99, 7388.
16. Wagner, P. J.; Sedon, J.; Waite, C., Gudmundsdottir, A J. Am. Chem. Soc. 1994, 116, 10284.
17. Scaiano, J. C.; Barra, M.; Krzywinski, M.; Sinta, R.; Calabrese, G. J. Am. Chem. Soc. 1993, 115, 8340.
18. Wagner, P. J.; Kochevar, I. E.; Kemppainen, A. E. J. Am. Chem. Soc. 1972, 94, 7489.
19. (a) Wagner, P. J.; McGrath, J. M. J. Am. Chem. Soc. 1972, 94, 3849
20. (b) Lewis, F. D.; Magyar, J. G. J. Am. Chem. Soc. 1973, 95, 5973.
21. (a) Wagner, P. J. J. Am. Chem. Soc. 1967, 89, 5898.
22. (b) Wagner, P J.; Kelso, P. A.; Kemppainen, A E.; McGrath, J. M.; Schott, H. N.; Zepp, R. G. J. Am. Chem. Soc. 1972, 94, 7506.
23. Wagner, P. J. In Handbook of Organic Photochemistry; Scaiano, J. C., Ed., CRC Press: Boca Raton, FL, 1989; Vol. 2, p 251.
24. McGimpsey, W. G.; Scaiano, J. C Can. J Chem. 1988, 66, 1474.
25. Arnold, D R Adv. Photochem. 1968, 6, 301.
26. (a) Kearns, D. R.; Case, W A. J. Am. Chem. Soc. 1966, 88, 5087.
27. (b) Yang, N. C.; McClure, D. S ; Murov, S. L , Houser, J. J., Dusenbery, R. J Am. Chem. Soc. 1967, 89, 5466.
28. Wagner, P. J., Kemppainen, A. E ; Schon, H. N. J. Am. Chem. Soc. 1973, 95, 5604
29. Wagner, P. J.; May, M J., Haug, A., Graber, D. R. J. Am. Chem. Soc 1970, 92, 5269.
30. (a) Clark, W. D K.; Litt, A. D.; Steel, C. J. Am. Chem Soc 1969, 91, 5413.
31. (b) Wagner, P J.; Kochevar, I. J. Am. Chem. Soc. 1968, 90, 2232.
32. (c) Scaiano, J. C.; Leigh, W. J ; Meador, M. A.; Wagner, P J. J. Am. Chem. Soc. 1985, 107, 5806.
33. Jacques, P , Lougnot, D. J ; Fouassier, J. P.; Scaiano, J. C. Chem. Phys. Lett. 1986, 127, 469
34. (a) Ermolaev, V L., Svitashev, K. K. Opt. Spectrosc 1959, 7, 399. See: Birks, J. B. Photophysics of Aromatic Molecules: Wiley: London, 1970, p 264.
35. (a) Ermolaev, V L., Svitashev, K. K. Opt. Spectrosc 1959, 7, 399. See: Birks, J. B. Photophysics of Aromatic Molecules: Wiley: London, 1970, p 264.
36. (b) Hoffman, M. Z ; Porter, G. Proc. R. Soc. Londond Ser. A 1962, 288, 46.
37. Wagner, P. J , Kelso, P. A.; Kemppainen, A. E., McGrath, J. M.; Scholl, H N ; Zepp, R. G. J. Am. Chem Soc. 1972, 94, 7506.
38. McGimpsey, W G.; Scaiano, J C. Can J Chem. 1988, 66, 1474.
39. Scaiano, J. C.; Stewart, L. C. J. Am. Chem. Soc. 1983, 105, 3609.
40. Zepp, R. G.; Wagner, P. J. J. Chem. Soc., Chem. Commun. 1972, 167 Guttenplan, J. B., Cohen, S. G. J. Org. Chem. 1973, 38, 2001.
41. Zepp, R. G.; Wagner, P. J. J. Chem. Soc., Chem. Commun. 1972, 167 Guttenplan, J. B., Cohen, S. G. J. Org. Chem. 1973, 38, 2001.
42. Wagner, P J.; Truman, R. J.; Puchalski, A. E.; Wake, R. J. Am. Chem. Soc. 1986, 108, 7727.
43. Berger, M.; McAlpine, E.; Steel, C. J. Am. Chem. Soc 1978, 100, 5147.
44. (a) Benson, S. W. Thermochemical Kinetics, 2nd ed.; Wiley: New York, 1976
45. (b) Egger, K W.; Cocks, A. T. Helv. Chem. Acta 1973, 56, 1516.
46. (c) McMillen, D. F.; Golden, D. M. Annu. Rev. Phys. Chem. 1982, 33, 493.
47. Wagner, P. J., Thomas, M. J.; Harris, E. J. Am. Chem. Soc 1976, 98, 7675.
48. Benson, S. W. Thermochemical Kinetics; Wiley: New York, 1968.
49. Zepp, R. G.; Wagner, P J J. Chem. Soc., Chem. Commun. 1972, 167.
50. Andrieux, C P.; Saveant, J.-M.; Su, K. B. J. Phys. Chem. 1986, 90, 3815.
51. Michl, J. Fortschr. Chem. Forsch. 1974, 46, 1.
52. Dauben, W. G., Salem, L., Turro, N. J. Acc. Chem. Res. 1975, 8, 41.
53. Encina, M. V , Lissi, E A.; Lemp, E ; Zanocco, A.; Scaiano, J. C. J. Am. Chem. Soc. 1983, 105, 1856
54. Rieger, P H.; Fraenkel, G. K. J. Chem. Phys. 1962, 37, 2795.
55. Mucha, J. A , Pratt, D. W J Chem. Phys. 1974, 66, 5339
56. (a) Hirota, N.; Wong, T. C.; Harrigan, E. T., Nishimoto, K. Mol. Phys. 1973, 29, 903.
57. (b) Wagner, P. J.; May, M. J. Chem Phys. Lett. 1976, 39, 350.
58. (c) Wagner, P J.; Siebert, E. J. J. Am. Chem. Soc. 1981, 103, 7329.
59. (a) Turro, N J., Schore, N. E.; Steinmetzer, H. C.; Yekta, A. J. Am. Chem. Soc. 1974, 96, 1936
60. (b) Mirbach, M F.; Ramamurthy, V., Mirbach, M. J.; Turro, N. J.; Wagner, P. J. Nouv. J. Chim. 1980, 4, 471.
61. Cao, Q. Ph.D. Thesis, Michigan State University, 1991.
62. (a) Wagner, P J., Chen, C.-P J. Am. Chem. Soc. 1976, 98, 239.
63. (b) Wagner, P. J. Pure Appl. Chem. 1977, 49, 159.
64. (a) Hauser, C. R., Humphlett, W J.; Weiss, M. J. J. Am. Chem. Soc. 1948, 70, 426.
65. (b) Wagner, P. J.; Kemppainen, A. E. J. Am. Chem. Soc. 1972, 94, 7495.
66. Allen, R. E.; Schumann, E. L.; Day, W C. J. Am. Chem. Soc. 1958, 80, 591.
67. Ogata, Y.; Tsuchida, M. J. Org. Chem. 1955, 20, 1631.
68. Scaiano, J. C. J. Am. Chem. Soc. 1980, 102, 7747.