Formation of σ- and π-type dimer radical cations by the photochemical one-electron oxidation of aromatic sulfides

Journal of the American Chemical Society

Volumn 120, Issue 49, 1998, Pages 12728-12733

  Yokoi, Hajime ^a   Hatta, Akio ^a   Ishiguro, Katsuya ^a   Sawaki, Yasuhiko ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; ANISOLE DERIVATIVE; AROMATIC COMPOUND; CATION; DIMER; NAPHTHALENE DERIVATIVE; RADICAL; SULFIDE;

ARTICLE; CHEMICAL BOND; ELECTRON TRANSPORT; MOLECULAR INTERACTION; MOLECULAR STABILITY; OXIDATION; PHOTOCHEMISTRY;

EID: 0032539220     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja982595s     Document Type: Article

References (61)

1. (a) Fox, M. A.; Chanon, M., Eds. Photoinduced Electron Transfer, Elsevier: Amsterdam, 1988; Parts A-D.
2. (b) Mattay, J. Synthesis 1989, 233-252.
3. (c) Bauld, N. L. Tetrahedron 1989, 45, 5307-5363.
4. (d) Bauld, N. L. Adv. Electron-Transfer Chem. 1992, 2, 1-66.
5. (e) Yoon, U. C.; Mariano, P. S. Ace. Chem. Res. 1992, 25, 233-240.
6. (f) Roth, H. D. Top. Curr. Chem. 1992, 163, 133-245.
7. Gould, I. R.; Farid, S. J. Am. Chem. Soc. 1993, 115, 4814-4822.
8. Vauthey, E. J. Phys. Chem. A 1997, 101, 1635-1639.
9. (a) Mizuno, K.; Kagano, H.; Kasuga, T.; Otsuji, Y. Chem. Lett. 1983, 133-136.
10. (b) Grellmann, K. H.; Suckow, U. Chem. Phys. Lett. 1975, 32, 250-254.
11. (c) Rodgers, M. A. J. J. Chem. Soc., Faraday Trans, 1 1972, 68, 1278-1286.
12. (d) Beens, H.; Weller, A. Chem. Phys. Lett. 1968, 2, 140-142.
13. Terahara, A.; Ohya-Nishiguchi, H.; Hirota, N.; Oku, A. J. Phys. Chem. 1986, 90, 1564-1571 and references therein.
14. Tojo, S.; Morishima, K.; Ishida, A.; Majima, T.; Takamuku, S. Bull. Chem. Soc. Jpn. 1995, 65, 958-966.
15. (a) Carmichael, I. Acta Chem. Scand. 1997, 51, 567-571.
16. (b) Mayer, P. M.; Keister, J. W.; Bear, T.; Evans, M.; Ng, C. Y.; Hsu, C.-W. J. Phys. Chem. A 1997, 101, 1270-1276.
17. (c) Maity, D. K.; Mohan, H.; Chattopadhyay, S.; Mittal, J. P. J. Phys. Chem. 1995, 99, 12195-12203.
18. (d) Shoute, L.'C. T.; Neta, P. J. Phys. Chem. 1991, 95, 4411-4414.
19. (e) Livant, P.; Illies, A. J. Am. Chem. Soc. 1991, 113, 1510-1513.
20. (f) Gebicki, J.; Marcinek, A.; Stradowski, C. J. Phys. Org. Chem. 1990, 3, 606-610.
21. (g) Schneider, S.; Geiselhart, P.; Seel, G.; Lewis, F. D.; Dykstra, R. E.; Nepras, M. J. J. Phys. Chem. 1989, 93, 3112-3117.
22. (h) Symons, M. C. R.; Chandra, H.; Alder, R. W. J. Chem. Soc., Chem. Commun. 1988, 844-845.
23. (i) Gandhi, N.; Wyatt, J. L.; Symons, M. C. R. J. Chem. Soc. Chem. Commun. 1986, 1424-1425.
24. (j) Hub, W.; Schneider, S.; Dörr, F.; Oxman, J. D.; Lewis, F. D. J. Am. Chem. Soc. 1984, 106, 701-708.
25. (k) Hub, W.; Schneider, S.; Dörr, F.; Oxman, J. D.; Lewis, F. D. J. Phys. Chem. 1983, 87, 4351-4353.
26. (a) Schneider, S.; Geiselhart, P.; Seel, G.; Lewis, F. D.; Dykstra, R. E.; Nepras, M. J. J. Phys. Chem. 1989, 93, 3112-3117.
27. (b) Lewis, F. D.; Kojima, M. J. Am. Chem. Soc. 1988, 110, 8664-8670.
28. (c) Ledwith, A. Acc. Chem. Res. 1972, 5, 133-139.
29. (a) Chaudhri, S. A.; Mohan, H.; Anklam, E.; Asmus, K.-D. J. Chem. Soc., Perkin. Trans. 2 1996, 383-390.
30. (b) James, M. A.; McKee, M. L.; Illies, A. J. J. Am. Chem. Soc. 1996, 118, 7836-7842.
31. (c) Sulfer-Centered Reactive Intermediates in Chemistry and Biology; Chatgilialoglu, C., Asmus, K.-D. Eds.; Plenum Press: New York, 1990.
32. (d) Mönig, J.; Goslich, R.; Asmus, K.-D. J. Phys. Chem. 1986, 90, 115-121.
33. (e) Bonifacic, M.; Asmus, K.-D. J. Chem. Soc., Perkin 2 1980, 758-762.
34. (f) Asmus, K.-D. Ace. Chem. Res. 1979, 12, 436-442.
35. (g) Gilbert, B. C.; Hodgeman, D. K. C.; Norman, R. O. J. Chem. Soc., Perkin. Trans. 2 1973, 1748-1752.
36. (a) Schöneich, C.; Asmus, K.-D.; Bonifacic, M. J. Chem. Soc., Faraday Trans. 1995, 91, 1923-1930.
37. (b) Wardman, P. In Sulfur Centered Reactive Intermediates in Chemistry and Biology, Chatgilialoglu, C., Asmus, K.-D., Eds.; NATO Ser. A, 197; Plenum Press: New York, 1990; p 415.
38. (c) Wardman, P. In Glutathione Conjugation; Sies, H., Ketterer, B., Eds.; Academic Press: New York, 1988; p 43.
39. (d) Sonntag, C. von. The Chemical Basis of Radiation Biology; Taylor and Francis: London, 1987.
40. ̇+ at 520 nm.
41. Bonifacic, M.; Möckel, H.; Bahnemann, D.; Asmus, K.-D. J. Chem. Soc., Perkin 2 1975, 675-685.
42. Chaudhri, S. A.; Göbi, M.; Freyholdt, T.; Asmus, K.-D. J. Am. Chem. Soc. 1984, 106, 5988-5992.
43. These Sulfides (1b and 1c) have a weak absorption band at 308 nm, then we use CA as a electron-accepting sensitizer to avoid direct irradiation of sulfides.
44. (a) Asmus, K.-D.; Bahnemann, D.; Fischer, C.-H.; Veitwisch, D. J. Am. Chem. Soc. 1979, 101, 5322-5329.
45. (b) Asmus, K.-D. Acc. Chem. Res. 1979, 12, 436-442.
46. Mohan, H.; Mittal, J. P. J. Phys. Chem. A 1997, 101, 10012-10017.
47. Hiyama, F. J. Chem. Phys. 1965, 42, 3163-3171.
48. (a) Sodupe, M.; Oliva, A.; Bertran, J. J. Am. Chem. Soc. 1995, 117, 8416-8421.
49. (b) Deng, Y.; Illies, A. J.; James, M. A.; McKee, M. L.; Peschke, M. J. Am. Chem. Soc. 1995, 117, 420-428.
50. (c) Ekem, S.; Illies, A. J.; McKee, M. L.; Peschke, M. J. Am. Chem. Soc. 1993, 115, 12510-12518.
51. James, M. A.; Illies, A. J. J. Phys. Chem. 1996, 100, 15794-15799.
52. (a) Neusser, H. J.; Krause, H. Chem. Rev. 1994, 94, 1829-1843.
53. (b) Ernstberger, B.; Krause, H.; Kiermeir, A.; Neusser, H. J. J. Chem. Phys. 1990, 92, 5285-5296.
54. (c) Meot-Ner (Mautner), M. J. Phys. Chem. 1980, 84, 2724-2728.
55. (d) Meot-Ner (Mautner), M.; Hamlet, P.; Hunter, E. P.; Field, F. J. Am. Chem. Soc. 1978, 100, 5466-5471.
56. Heiss, L.; Paulus, E. F.; Rehling, H. Liebigs Ann. Chem. 1980, 1583-1596.
57. (a) Mann, F. G.; Purdie, D. J. Chem. Soc. 1935, 1549-1563.
58. (b) Tanaka, K.; Uneme, H.; Matsui, S.; Tanikaga, R.; Kaji, A. Chem. Lett. 1980, 287-288.
59. Jeminet, G.; Kergomard, A. C. R. Acad. Sci., Paris, Ser. C 1967, 264, 614-617.
60. Nojima, T.; Ishiguro, K.; Sawaki, Y. J. Org. Chem. 1997, 62, 6911-6917.
61. Chaudhri, S. A.; Göbi, M.; Freyholdt, T.; Asmus, K.-D. J. Am. Chem. Soc. 1984, 106, 5988-5992.