Redox reaction of benzyl radicals with aromatic radical ions photogenerated. The Marcus inverted region and the selective formation of carbocations or carbanions

Journal of the American Chemical Society

Volumn 118, Issue 31, 1996, Pages 7255-7264

  Ishiguro, Katsuya ^a   Nakano, Tomoharu ^a   Shibata, Hiroki ^a   Sawaki, Yasuhiko ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; RADICAL;

ARTICLE; OXIDATION REDUCTION REACTION; PHOTOCHEMISTRY; REACTION ANALYSIS;

EID: 0029759524     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953689u     Document Type: Article

References (123)

1. (a) Fry, A. J. In Synthetic Organic Electrochemistry; Wiley. New York, 1989; p 60.
2. (b) Amatore, C. In Organic Electrochemistry; Lund, H., Baizer, M. M., Eds.; Marcel Dekker. New York, 1991; p 76.
3. (a) Kavarnos, G. J.; Turro, N. J. Chem. Rev. 1986, 86, 401.
4. (b) Photoinduced Electron Transfer, Fox, M. A., Chanon, M., Eds.; Elsevier: Amsterdam, 1988.
5. (a) Arnold, D. R.; Maroulis, A. J. J. Am. Chem. Soc. 1976, 98, 5931.
6. (b) Okamoto, A.; Snow, M. S.; Arnold, D. A. Tetrahedron 1986, 42, 6175.
7. (c) Arnold. D. R.; Lamont, L. Can. J. Chem. 1989, 67, 2119.
8. (d) Popielarz, R.; Arnold, D. R. J. Am. Chem. Soc. 1990, 112, 3068.
9. (e) Albini, A.; Mella, M.; Freccero, M. Tetrahedron 1994, 50, 575.
10. (a) Shigemitsu, Y.; Arnold, D. R. J. Chem. Soc., Chem. Commun. 1975, 407.
11. (b) Gassman, P. G.; Bottorff, K. J. J. Am. Chem. Soc. 1987, 109, 7547.
12. Gassman, P. G.; De Silva, S. A. J. Am. Chem. Soc. 1991, 113, 9870.
13. (a) Marcus, R. A. J. Chem. Phys. 1956, 24, 966.
14. (b) Marcus, R. A. Annu. Rev. Phys. Chem. 1964, 15, 155.
15. (c) Eberson, L. In Advances in Physical Organic Chemistry; Gold, V., Bethell, D., Eds.; Academic Press: London, 1982; Vol. 18, p 10.
16. Miller, J. R.; Calcaterra, L. T.; Closs, G. L. J. Am. Chem. Soc. 1984, 106, 3047.
17. Wasielewski, M. R.; Niemczyk, M. P.; Svec, W. A.; Pewitt, E. B. J. Am. Chem. Soc. 1985, 107, 1080.
18. (a) Beitz, J. V.; Miller, J. R. J. Chem. Phys. 1979, 71, 4579.
19. (b) Miller, J. R.; Beitz, J. V.; Huddleston, R. K. J. Am. Chem. Soc. 1984, 106, 5057.
20. Levin, P. P.; Pluzhnikov, P. F.; Kuzmin, V. A. Chem. Phys. Lett. 1988, 147, 283.
21. (a) Gould, I. R.; Ege, D.; Mattes, S. L.; Farid, S. J. Am. Chem. Soc. 1987, 109, 3794.
22. (b) Gould, I. R.; Moser, J. E.; Ege, D.; Farid, S. J. Am. Chem. Soc. 1988, 110, 1992.
23. (c) Gould, I. R.; Moser, J. E.; Armitage, B.; Farid, S.; Goodman, J. L.; Herman, M. S. J. Am. Chem. Soc. 1989, 111, 1917.
24. (d) Gould, I. R.; Ege, D.; Moser, J. E.; Farid, S. J. Am. Chem. Soc. 1990, 112, 4290.
25. (a) Ohno, T.; Yoshimura, A.; Mataga, N. J. Phys. Chem. 1986, 90, 3295.
26. (b) Mataga, N.; Asahi, T.; Kanda, Y.; Okada, T.; Kakitani, T. Chem. Phys. 1988, 127, 249.
27. Vauthey, E.; Suppan, P.; Haselbach, E. Helv. Chim. Acta 1988, 71, 93.
28. Kikuchi, K.; Takahashi, Y.; Koike, K.; Wakamatsu, K.; Ikeda, H.; Miyashi, T. Z. Phys. Chem. (Munich) 1990, 167, 27.
29. Grampp, G.; Hetz, G. Ber. Busenges. Phys. Chem. 1992, 96, 198.
30. (a) Gould, I. R.; Moody, R.; Farid, S. J. Am. Chem. Soc. 1988, 110, 7242.
31. (b) Gould, I. R.; Young, R. H.; Moody, R. E.; Farid, S. J. Phys. Chem. 1991, 95, 2068.
32. (a) Asahi, T.; Mataga, N. J. Phys. Chem. 1989, 93, 6575.
33. (b) Asahi, T.; Mataga, N. J. Phys. Chem. 1991, 95, 1956.
34. Zou, C.; Miers, J. B.; Ballew, R. M.; Dlott, D. D.; Schuster, G. B. J. Am. Chem. Soc. 1991, 113, 7823.
35. (a) DeCosta, D. P.; Pincock, J. A. J. Am. Chem. Soc. 1989, 111, 8948; 1993, 115, 2180.
36. (a) DeCosta, D. P.; Pincock, J. A. J. Am. Chem. Soc. 1989, 111, 8948; 1993, 115, 2180.
37. (b) Hilborn, J. W.; MacKnight, J. A.; Pincock, J. A.; Wedge, P. J. J. Am. Chem. Soc. 1994, 116, 3337.
38. Rehm, D.; Weller, A. Isr. J. Chem. 1970, 8, 259.
39. (b) Nishikawa, S.; Asahi, T.; Okada, T.; Mataga, N.; Kakitani, T. Chem. Phys. Lett. 1991, 185, 237.
40. (a) Suppan, P. Top. Curr. Chem. 1992, 163, 95.
41. (b) Grampp, G. Angew. Chem., Int. Ed. Engl. 1993, 32, 691.
42. Schomberg, H.; Staerk, H.; Weller, A. Chem. Phys. Lett. 1973, 21, 433; 1973, 22, 2735.
43. Schomberg, H.; Staerk, H.; Weller, A. Chem. Phys. Lett. 1973, 21, 433; 1973, 22, 2735.
44. Gschwind, R.; Haselbach, E. Helv. Chim. Acta 1979, 62, 941.
45. Delcourt, M. O.; Rossi, M. J. J. Phys. Chem. 1982, 86, 3233.
46. Kakitani, T.; Mataga, N. Chem. Phys. 1985, 93, 381; J. Phys. Chem. 1985, 89, 4752; Chem. Phys. Lett. 1986, 124, 437.
47. Kakitani, T.; Mataga, N. Chem. Phys. 1985, 93, 381; J. Phys. Chem. 1985, 89, 4752; Chem. Phys. Lett. 1986, 124, 437.
48. Kakitani, T.; Mataga, N. Chem. Phys. 1985, 93, 381; J. Phys. Chem. 1985, 89, 4752; Chem. Phys. Lett. 1986, 124, 437.
49. (a) Kakitani, T.; Yoshimori, A.; Mataga, N. J. Phys. Chem. 1992, 96, 5385.
50. (b) Tachiya, M.; Murata, S. J. Phys. Chem. 1992, 96, 8441.
51. (a) Wayner, D. D. M.; McPhee, D. J.; Griller, D. J. Am. Chem. Soc. 1988, 110, 132.
52. (b) Sim, B. A.; Milne, P. H.; Griller, D.; Wayner, D. D. M. J. Am. Chem. Soc. 1990, 112, 6635.
53. Gould, I. R.; Baretz, B. H.; Turro, N. J. J. Phys. Chem. 1987, 91, 925.
54. (a) Robbins, W. K.; Eastman, R. H. J. Am. Chem. Soc. 1970, 92, 6076.
55. (b) Engel, P. S. J. Am. Chem. Soc: 1970, 92, 6074.
56. Das, P. K. Chem. Rev. 1993, 93, 119 and references cited therein.
57. •-, however, are governed by the back electron transfer and we have no information about the true yields for free ions for various D-A pairs in the tables, (b) Grellmann, K. L.; Watkins, A. R.; Weller, A. J. Phys. Chem. 1972, 76, 469.
58. •-, however, are governed by the back electron transfer and we have no information about the true yields for free ions for various D-A pairs in the tables, (b) Grellmann, K. L.; Watkins, A. R.; Weller, A. J. Phys. Chem. 1972, 76, 469.
59. •+ with methanol seems not to be significant since the resulting yields of oxidized product were rather constant when changing the amount of MeOH from 3 to 20%.
60. (b) Zevos, N.; Sehested, K. J. Phys. Chem. 1978, 82, 138.
61. (c) Steenken, S.; Warren, J.; Gilbert, B. C. J. Chem. Soc., Perkin Trans. 2 1990, 335.
62. Lusztyk, J., Kanabus-Kaminska, J. M. In Handbook of Organic Photohemistry; Scaiano, J. C., Ed.; CRC Press: Boca Raton, 1989; Vol. 2, Chapter 8.
63. (a) Sujdak, R. J.; Jones, R. L.; Dorfman, L. M. J. Am. Chem. Soc. 1976, 98, 4875.
64. (b) McClelland, R. A.; Kanagasabapathy, V. M.; Banait, N.; Steenken, S. J. Am. Chem. Soc. 1989, 111, 3966.
65. (c) Bockrath, B.; Dorfman, L. M. J. Am. Chem. Soc. 1975, 97, 3307.
66. Tsuchida, A.; Tsuji, Y.; Ito, S.; Yamamoto, M.; Wada, Y. J. Phys. Chem. 1989, 93, 1244.
67. Redox potentials of benzyl ketones were determined by rotating ring-disk electrode voltammetry as listed in Table 1.
68. Lipson, M.; Noh, T.; Doubleday, C.; Zaleski, J. M.; Turro, N. J. J. Phys. Chem. 1994, 98, 8844.
69. (a) Lunazi, L.; Ingold, K. U.; Scaiano, J. C. J. Phys. Chem. 1983, 87, 529.
70. (b) Turro, N. J.; Gould, I. R.; Baretz, B. H. J. Phys. Chem. 1983, 87, 531.
71. Fagnoni, M.; Mella, M.; Albini, A Tetrahedron 1994, 50, 6401.
72. Arnold, D. R.; Maroulis, A. J. J. Am. Chem. Soc. 1977, 99, 7355.
73. Johnston, L. J.; Kanigan, T. J. Am. Chem. Soc. 1990, 112, 1271.
74. (a) Sehested, K.; Corfitzen, H.; Christiansen, H. C.; Hart, E. J. J. Phys. Chem. 1975, 79, 310.
75. (b) Sehested, K.; Holcman, J.; Hart, E. J. J. Phys. Chem. 1977, 81, 1363.
76. Gould, I. R.; Farid, S. J. Am. Chem. Soc. 1993, 115, 4814.
77. See ref 6c, p 79.
78. Lewis, F. D.; Bedell, A. M.; Dykstra, R. E.; Elbert, J. E.; Gould, I. R.; Farid, S. J. Am. Chem. Soc. 1990, 112, 8055.
79. Gould, I. R.; Farid, S. J. Phys. Chem. 1993, 97, 13067.
80. Kikuchi, K.; Katagiri, T.; Niwa, T.; Takahashi, Y.; Suzuki, T.; Ikeda, H.; Miyashi, T. Chem. Phys. Lett. 1992, 193, 155.
81. Marcus, R. A.; Siders, P. J. Phys. Chem. 1982, 86, 622.
82. Kikuchi, K.; Niwa, T.; Takahashi, Y.; Ikeda, H.; Miyashi, T. J. Phys. Chem. 1993, 97, 5070.
83. Kikuchi, K.; Takahashi, Y.; Hoshi, M.; Niwa, T.; Katagiri, T.; Miyashi, T. J. Phys. Chem. 1991, 95, 2378.
84. Miyasaka, H.; Monta, K.; Kamada, K.; Nagata, T.; Kiri, M.; Mataga, N. Bull. Chem. Soc. Jpn. 1991, 64, 3229.
85. Gschwind, R.; Haselbach, E. Helv. Chim. Acta 1979, 62, 941.
86. Schomberg, H.; Staerk, H.; Weller, A. Chem. Phys. Lett. 1973, 21, 433; 1973, 22, 2735.
87. Schomberg, H.; Staerk, H.; Weller, A. Chem. Phys. Lett. 1973, 21, 433; 1973, 22, 2735.
88. Delcourt, M. O.; Rossi, M. J. J. Phys. Chem. 1982, 86, 3233.
89. McCleckey, T. M.; Winkler, J. R.; Gray, H. B. J. Am. Chem. Soc. 1992, 114, 6935.
90. (a) Tachiya, M. J. Phys. Chem. 1989, 93, 7050.
91. (b) Kakitani, T. In Dynamics and Mechanism of Photoinduced Electron Transfer and Related Phenomena; Mataga, N., Okada, T., Masuhara, H., Eds.; Elsevier: Amsterdam, 1992; p 71.
92. Legros, B.; Vandereecken, P.; Soumillion, J. J. Phys. Chem. 1991, 95, 4752.
93. Eriksen, J.; Jørgensen, K. A.; Linderberg, J.; Lund, H. J. Am. Chem. Soc. 1984, 106, 5083.
94. Nagaoka, T.; Griller, D.; Wayner, D. D. M. J. Phys. Chem. 1991, 95, 6264.
95. (a) Fuhlendorff, R.; Occhialini, D.; Pedersen, S. U. Acta Chem. Scand. 1989, 43, 803.
96. (b) Occhialini, D.; Pedersen, S. U.; Lund, H. Acta Chem. Scand. 1990, 44, 715.
97. (c) Occhialini, D.; Kristensen, J. S.; Daasbjerg, K.; Lund, H. Acta Chem. Scand. 1992, 46, 474.
98. Mikkelsen, K. V.; Pedersen, S. U.; Lund, H.; Swanstrom, P. J. Phys. Chem. 1991, 95, 8892.
99. Nelsen, S. F.; Blackstock, S. C.; Kim, Y. J. Am. Chem. Soc. 1987, 109, 677.
100. Steiner, U. E.; Ulrich, T. Chem. Rev. 1988, 89, 51.
101. Saltiel, J.; Atwater, B. W. Adv. Photochem. 1988, 14, 1.
102. Bard, A. J.; Ledwith, A.; Shine, H. J. Adv. Phys. Org. Chem. 1976, 12, 155.
103. (a) Schaap, A. P.; Zaklika, K. A.; Kaskar, B.; Fung, L. W.-M. J. Am. Chem. Soc. 1980, 102, 389.
104. (b) Spada, L. T.; Foote, C. S. J. Am. Chem. Soc. 1980, 102, 391.
105. (a) Ci, X.; Kellett, M. A.; Whitten, D. G. J. Am. Chem. Soc. 1991, 113, 3893.
106. (b) Freccero, M.; Mella, M.; Albini, A. Tetrahedron 1994, 50, 2115.
107. Dean, D. O.; Dikinson, W. B.; Quayle, O. R.; Lester, C. T. J. Am. Chem. Soc. 1950, 72, 1740.
108. (a) Kimura, Y.; Tomiya, Y.; Nakanishi, S.; Otsuji, Y. Chem. Lett. 1979, 321.
109. (b) Turro, N. J.; Weed, G. C. J. Am. Chem. Soc. 1983, 105, 1861.
110. Meek, J. S.; Monroe, P. A.; Bouboulis, C. J. J. Org. Chem. 1963, 28, 2572.
111. Suzuki, H.; Hanafusa, T. Syntheses 1974, 1, 53.
112. Dufraisse, C. Bull. Soc Chim. Fr. 1947, 302.
113. Bard, A. J.; Faulkner, L. R. In Electrochemical Methods; Wiley: New York, 1980.
114. (a) Zweig, A.; Hodgson, W. G.; Jura, W. H. J. Am. Chem. Soc. 1964, 86, 4124.
115. (b) Zweig, A.; Hodgson, W. G.; Jura, W. H. J. Org. Chem. 1967, 32, 1322.
116. (c) Hamada, T.; Nishida, A.; Yonemitsu, O. J. Am. Chem. Soc. 1986, 108, 140.
117. MOPAC version 5.00 (QCPE No.445): Stewart, J. J. P. QCPE Bull. 1989, 9, 10. Hirano, T. JCPE Newsletter 1989, 1 (2), 36. Revised as version 5.01 for OS/2 Personal Computers (NEC PC-9801): Toyoda. J. JCPE Newsletter 1990, 2(1), 56.
118. MOPAC version 5.00 (QCPE No.445): Stewart, J. J. P. QCPE Bull. 1989, 9, 10. Hirano, T. JCPE Newsletter 1989, 1 (2), 36. Revised as version 5.01 for OS/2 Personal Computers (NEC PC-9801): Toyoda. J. JCPE Newsletter 1990, 2(1), 56.
119. MOPAC version 5.00 (QCPE No.445): Stewart, J. J. P. QCPE Bull. 1989, 9, 10. Hirano, T. JCPE Newsletter 1989, 1 (2), 36. Revised as version 5.01 for OS/2 Personal Computers (NEC PC-9801): Toyoda. J. JCPE Newsletter 1990, 2(1), 56.
120. MOPAC version 5.00 (QCPE No.445): Stewart, J. J. P. QCPE Bull. 1989, 9, 10. Hirano, T. JCPE Newsletter 1989, 1 (2), 36. Revised as version 5.01 for OS/2 Personal Computers (NEC PC-9801): Toyoda. J. JCPE Newsletter 1990, 2(1), 56.
121. MOPAC version 6.00 (QCPE No.445): Stewart, J. J. P. QCPE Bull. 1990, 10, 86. Version 6.02: Hirano, T. JCPE Newsletter 1991, 2 (4), 39. Macintosh version: Toyota, J., 1991.
122. MOPAC version 6.00 (QCPE No.445): Stewart, J. J. P. QCPE Bull. 1990, 10, 86. Version 6.02: Hirano, T. JCPE Newsletter 1991, 2 (4), 39. Macintosh version: Toyota, J., 1991.
123. MOPAC version 6.00 (QCPE No.445): Stewart, J. J. P. QCPE Bull. 1990, 10, 86. Version 6.02: Hirano, T. JCPE Newsletter 1991, 2 (4), 39. Macintosh version: Toyota, J., 1991.