Photosensitized electron transfer oxidation of sulfides: A steady-state study

European Journal of Organic Chemistry

Volumn , Issue 15, 2008, Pages 2612-2620

  Bonesi, Sergio M ^a,b   Fagnoni, Maurizio ^b   Albini, Angelo ^b  

^a Facultad de Ciencias Naturales e Instituto M Lillo   (Argentina)

^b UNIVERSITY OF PAVIA   (Italy)

Author keywords

Electron transfer; Oxidation; Photochemistry; Reaction mechanisms; Sulfides

Indexed keywords

EID: 53849136898     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800048     Document Type: Article

References (92)

1. J. Drabowicz, P. Kielbasinski, M. Mikolajczyk in Synthesis of Sulfones, Sulfoxides and Cyclic Sulfides (Eds.: S. Patai, Z. Rappoport), Wiley, Chichester, 1994, p. 195;
2. E. G. Mata, Phosphorus Sulfur Silicon Relat. Elem. 1996, 117, 231;
3. J. W. Chu, B. L. Trout, J. Am. Chem. Soc. 2004, 126, 900;
4. A. K. Das, Coord. Chem. Rev. 2004, 248, 81;
5. M. C. Carreño, Chem. Rev. 1995, 95, 1717;
6. A. L. Baumstark, Bioorg. Chem. 1986, 14, 326;
7. P. Filipiak, G. L. Hug, I. Charmichael, A. Korzeniowska-Sobczuk, K. Bobrowoski, B. Marciniak, J. Phys. Chem. A 2004, 108, 6503;
8. M. L. Huang, A. Rauk, J. Phys. Chem. 2004, 108, 6222.
9. a) E. Baciocchi, C. Crescenzi, O. Lanzalunga, Tetrahedron 1997, 53, 4469;
10. b) J. Eriksen, C. S. Foote, T. L. Parker, J. Am. Chem. Soc. 1977, 99, 6455;
11. c) N. Soggiu, H. Cardy, J. L. Habib, J. P. Soumillon, J. Photochem. Photobiol. A 1999, 124, 1; d)
12. e) Y. Che, W. Ma, Y. Ren, C. Chen, X. Zhang, J. Zhao, L. Zang, J. Phys. Chem. B 2005, 109, 8270;
13. f) S. Lacombe, H. Cardy, M. Simon, A. Khoukh, J. P. Soumillon, M. Ayadim, Photochem. Photobiol. Sci. 2002, 1, 347;
14. g) T. Pigot, T. Arbitre, M. Hervé, S. Lacombe, Tetrahedron Lett. 2004, 45, 4047;
15. h) V. Latour, T. Pigot, M. Simon, H. Cardy, S. Lacombe, Photochem. Photobiol. Sci. 2005, 4, 221;
16. K. Bobrowski, B. Marciniak, G. L. Hug, J. Photochem. Photobiol. A 1994, 81, 159;
17. S. Inbar, H. Linschitz, S. G. Cohen, J. Am. Chem. Soc. 1982, 104, 1679;
18. J. C. Ronfard-Haret, R. V. Bensasson, J. C. Gramain, Chem. Phys. Lett. 1983, 96, 31;
19. W. Adam, J. E. Arguello, A. B. Penenory, J. Org. Chem. 1998, 63, 3905;
20. E. Bosch, J. K. Kochi, J. Org. Chem. 1995, 60, 3172;
21. V. Iliev, D. Tomova, Catal. Commun. 2002, 3, 287;
22. M. Alvaro, E. Carbonell, H. Garcia, Appl. Catal. B 2004, 51, 195.
23. E. L. Clennan, Acc. Chem. Res. 2001, 34, 875;
24. E. L. Clennan, Sulfur Rep. 1996, 19, 171;
25. E. L. Clennan, C. Liao, Tetrahedron 2006, 62, 10724;
26. E. L. Clennan, S. E. Hightower, A. Greer, J. Am. Chem. Soc. 2005, 127, 11819.
27. T. Akasaka, W. Ando, Tetrahedron Lett. 1985, 26, 5049.
28. E. Baciocchi, T. Del Giacco, F. Elisei, M. F. Gerini, M. Guerra, A. Lapi, P. Liberali, J. Am. Chem. Soc. 2003, 125, 16444;
29. E. Baiocchi, T. Del Giacco, P. Giombolini, O. Lanzalunga, Tetrahedron 2006, 62, 6566;
30. Y. Che, W. Ma, Y. Ren, C. Chen, X. Zhang, J. Zhao, L. Zang, J. Phys. Chem. B 2005, 109, 8270.
31. S. M. Bonesi, I. Manet, M. Freccero, M. Fagnoni, A. Albini, Chem. Eur. J. 2006, 12, 4844.
32. a) D. C. Dobrowolski, P. R. Ogilby, C. S. Foote, J. Phys. Chem. 1983, 87, 2261;
33. b) R. S. Davidson, J. E. Pratt, Tetrahedron 1984, 40, 999;
34. c) L. E. Manring, C. L. Gu, C. S. Foote, J. Phys. Chem. 1983, 87, 40;
35. d) A. P. Darmanyan, Chem. Phys. Lett. 1984, 110, 89;
36. e) W. Abraham, A. Glänzel, R. Stösser, U. W. Grummt, H. Köppel, J. Photochem. Photobiol. 1990, 51, 350.
37. D. T. Breslin, M. A. Fox, J. Am. Chem. Soc. 1993, 115, 11716.
38. a) R. D. Egland, F. Marken, E. M. Southern, Anal. Chem. 2002, 74, 1590;
39. b) M. A. Fox, M. Chanon (Eds.), Photoinduced Electron Transfer, Elsevier, Amsterdam, 1988, p. 475.
40. a) F. D. Saeva, G. R. Olin, J. Am. Chem. Soc. 1980, 102, 299;
41. b) R. Akaba, H. Sakuragi, K. Tokumaru, J. Chem. Soc. Perkin Trans. 2 1991, 291;
42. c) M. A. Miranda, H. Garcia, Chem. Rev. 1994, 94, 1063;
43. d) K. D. Warzecha, M. Demuth, H. Görner, J. Chem. Soc. Faraday Trans. 1997, 93, 1523;
44. e) M. V. Baldovi, H. Garcia, M. A. Miranda, J. Primo, J. Soto, F. Vargas, Tetrahedron 1995, 51, 8113.
45. [5b]).
46. 2/εa term is disregarded as no charge separation is involved.
47. b) D. Rehm, A. Weller, Isr. J. Chem. 1970, 8, 259.
48. As an example of the ionization potential of the ethyl radical, values between 8.11 and 8.24 eV have been reported, see: a) B. Ruscic, J. Berkowitz, L. A. Curtiss, J. A. Pople, J. Chem. Phys. 1989, 91, 114;
49. b) J. Wang, L. Wei, B. Yang, R. Yang, C. Huang, X. Shan, L. Sheng, Y. Zhang, F. Qi, C. Yao, Q. Li, Q. Ji, Chem. Res. Chin. Univ. 2006, 22, 375;
50. .) ≈ 1.00 V vs. SCE were estimated from the measured IP by the Miller equation, not taking into account the solvation energy which may heavily affect the result.
51. M. Ioele, S. Steenken, E. Baciocchi, J. Phys. Chem. A 1997, 101, 2979;
52. E. Baciocchi, M. F. Gerini, O. Lanzalunga, A. Lapi, M. G. Lo Piparo, Org. Biomol. Chem. 2003, 1, 422.
53. 2CHSPh, see: F. G. Bordwell, X. Zhang, J. P. Cheng, J. Org. Chem. 1991, 56, 3216;
54. lower values were proposed for related derivatives, see: E. Baciocchi, C. Rol, E. Scamosci, G. V. Sebastiani, J. Org. Chem. 1991, 56, 5498.
55. In related compounds it was found that the C-H energy changes by ≤1 kcal/mol when an EtS is substituted for a PhS group: F. G. Bordwell, X. M. Zhang, J. Am. Chem. Soc. 1994, 116, 973.
56. .+ and thus BDFE reasonably negative for both radical cations.
57. See, for example: a) M. Freccero, A. Pratt, A. Albini, C. Long, J. Am. Chem. Soc. 1998, 120, 284;
58. b) E. Baciocchi, M. Bietti, O. Lanzalunga, J. Phys. Org. Chem. 2006, 19, 467.
59. -1.
60. +, viable, see: T. Lund, D. D. M. Wayner, M. Jonsson, A. G. Larsen, K. Daasbjerg, J. Am. Chem. Soc. 2001, 123, 12590.
61. a) S. M. Bonesi, M. Fagnoni, S. Monti, A. Albini, Tetrahedron 2006, 62, 10716;
62. b) S. M. Bonesi, M. Mella, N. d'Alessandro, G. G. Aloisi, M. Vanossi, A. Albini, J. Org. Chem. 1998, 63, 9946.
63. J. J. Liang, C. L. Gu, M. L. Kacher, C. S. Foote, J. Am. Chem. Soc. 1983, 105, 4717;
64. E. L. Clennan, A. Greer, J. Org. Chem. 1996, 61, 4793;
65. F. Jensen, A. Greer, E. L. Clennan, J. Am. Chem. Soc. 1998, 120, 4439;
66. E. L. Clennan, D. Wang, C. Clifton, M. F. Chen, J. Am. Chem. Soc. 1997, 119, 9081.
67. A. Toutchine, D. Aebischer, E. L. Clennan, J. Am. Chem. Soc. 2001, 123, 4996.
68. a) W. Ando, Y. Kabe, S. Kobayashi, C. Takyu, A. Yamagishi, H. Inaba, J. Am. Chem. Soc. 1980, 102, 4526.
69. [5,6] although in every case subsequent paths from such intermediates to the sulfoxide are strongly exothermic.
70. T. Del Giacco, L. Lipparoni, M. Ranchella, C. Rol, G. V. Sebastiani, J. Chem. Soc. Perkin Trans. 2 2001, 1802.
71. B. Branchi, M. Bietti, G. Ercolani, M. A. Izquierdo, M. A. Miranda, J. Org. Chem. 2004, 69, 8874.
72. 2 is more competitive at the low flux of steady-state irradiation than in flash experiments.
73. [27] [26] D. Jacobi, W. Abraham, U. Pischel, L. Grubert, R. Stösser, W. Schnabbel, J. Chem. Soc. Perkin Trans. 2 1999, 1695.
74. M. Alvaro, E. Carbonell, H. Garcia, Appl. Catal., B 2004, 51, 195.
75. a) C. H. Tung, J. Q. Guan, J. Am. Chem. Soc. 1998, 120, 11874;
76. b) M. Kojima, A. Ishida, S. Takamuku, Bull. Chem. Soc. Jpn. 1998, 71, 2211;
77. c) T. Tamai, N. Ichinose, T. Tanaka, T. Sasuga, I. Hashida, K. Mizuno, J. Org. Chem. 1998, 63, 3204;
78. d) W. Adam, W. Haas, B. B. Lohray, J. Am. Chem. Soc. 1991, 113, 6202;
79. e) F. D. Lewis, M. Kojima, J. Am. Chem. Soc. 1988, 110, 8664.
80. a) E. A. Fehnel, M. Cormack, J. Am. Chem. Soc. 1949, 71, 84;
81. b) C. G. Skrettas, M. Mischa-Skrettas, J. Am. Chem. Soc. 1979, 44, 714.
82. J. Erikson, C. S. Foote, J. Am. Chem. Soc. 1980, 102, 6083.
83. a) A. Cerniani, G. Modena, P. G. Todesco, Gazz. Chim. Ital. 1960, 90, 3;
84. b) J. F. Carson, F. F. Wong, J. Org. Chem. 1959, 24, 175.
85. a) J. P. McCullough, H. L. Finke, W. N. Hubbard, S. S. Todd, J. F. Messerly, D. R. Doublin, G. Waddington, J. Phys. Chem. 1961, 65, 784;
86. b) A. J. Colussi, S. W. Benson, Int. J. Chem. Kinet. 1977, 9, 295.
87. D. H. Fine, J. B. Westmore, J. Chem. Soc. D 1969, 273.
88. E. T. Denisov, Russ. J. Phys. Chem. (Engl. Transl.) 1995, 69, 396.
89. T. Koizumi, T. Fuchigami, T. Nonaka Bull. Chem. Soc. Jpn. 1989, 62, 219.
90. D. M. Wayner, A. Houmam, Acta Chem. Scand. 1998, 52, 377.
91. S. P. Verevkin, E. L. Krasnykh, J. S. Wright, Phys. Chem. Chem. Phys. 2003, 5, 2605.
92. M. J. Rossi, D. F. McMillen, D. M. Golden, J. Phys. Chem. 1984, 88, 5031.