Electron transfer in organic reactions

Journal of Physical Organic Chemistry

Volumn 10, Issue 3, 1997, Pages 129-137

  Patz, Matthias ^a   Fukuzumi, Shunichi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Electron transfer; Electrophile; Mechanism; Nucleophile; Outer sphere electron transfer

Indexed keywords

EID: 0000247437     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1395(199703)10:3<129::AID-POC884>3.0.CO;2-4     Document Type: Review

References (114)

1. K. Maruyama, Bull. Chem. Soc. Jpn. 37, 897 (1964).
2. R. C. Kerber, G. W. Urry and N. Kornblum, J. Am. Chem. Soc. 86, 3904-3905 (1964).
3. G. A. Russell, E. G. Janzen and E. T. Strom, J. Am. Chem. Soc. 86, 1807-1814 (1964).
4. (a) J. K. Kochi, Angew. Chem., Int. Ed. Engl. 27, 1227-1258 (1988)
5. (b) S. Fukuzumi and J. K. Kochi, Bull. Chem. Soc. Jpn. 56, 969-979 (1983).
6. E. C. Ashby Acc. Chem. Res. 21, 414-421 (1988).
7. N. N. Semenov, Some Problems in Chemical Kinetics and Reactivity. Princeton University Press, Princeton, NJ (1958).
8. A. Pross,-Acc. Chem. Res. 18, 212-219 (1985).
9. (a) C. K. Ingold, J. Chem. Soc. 1120-1127 (1933)
10. (b) C. K. Ingold, Chem. Rev. 15, 225-274 (1934).
11. (a) R. A. Marcus, Angew. Chem. 105, 1161 -1180 (1993)
12. (b) R. A. Marcus, Annu. Rev. Phys. Chem. 15, 155-196 (1964).
13. (a) D. Rehm and A. Weller, Ber. Bunsenges. Phys. Chem. 73, 834-839 (1969)
14. (b) D. Rehm and A. Weller, Isr. J. Chem. 8, 259 (1970).
15. (a) T. Lund and H. Lund, Acta Chem. Scand., Ser. B 40, 470-485 (1986)
16. (b) C. P. Andrieux, I. Gallardo, J.-M. Savéant and K.-B. Su, J. Am. Chem. Soc. 108, 638-647 (1986).
17. (a) R. A. Marcus and P. Siders, J. Phys. Chem. 86, 622-630 (1982);
18. (b) P. Suppan, Top. Curr. Chem. 163, 95-130 (1992).
19. (a) T. M. McCleskey, J. R. Winkler and H. B. Gray, J. Am. Chem. Soc. 114, 6935-6937 (1992)
20. (b) M. Tachiya and S. Murata, J. Phys. Chem. 96, 8441-8444 (1992)
21. (c) T. Kakitani, A. Yoshimori and N. Mataga, J. Phys. Chem. 96, 5385-5392 (1992)
22. (d) J. Kroon, H. Oevering, J. W. Verhoeven, J. M. Warman, A. M. Oliver and M. N. Paddon-Row, J. Phys. Chem. 97, 5065-5069 (1993)
23. (e) B. Legros, P. Vandereecken and J. Ph. Soumillion, J. Phys. Chem. 95, 4752-4761 (1991).
24. C. Creutz and N. Sutin, J. Am. Chem. Soc. 99, 241-243 (1977).
25. K. C. Cho, C. M. Che, K. M. Ng and C. L. Choy, J. Phys. Chem. 91, 3690-3369 (1987).
26. L. Eberson, Electron Transfer in Organic Chemistry. Springer, Berlin (1987).
27. A. Williams, Chem. Soc. Rev. 23, 93-100 (1994).
28. R. Sustmann, K. Lücking, G. Kopp and M. Rese, Angew. Chem., Int. Ed. Engl. 28, 1713 (1989).
29. K. Maruyama and T. Katagiri, J. Am. Chem. Soc. 108, 6263-6270 (1986).
30. E. C. Ashby and J. N. Argyropoulos, J. Org. Chem. 51, 472-476 (1986).
31. (a) J. F. Johnston, J. R. Ridd and J. P. B. SDandall, J. Chem. Soc., Perkin Trans. 2 623-628 (1991)
32. (b) M. Lehnig, J. Chem. Soc., Perkin Trans. 2 1943-1948 (1996).
33. D. Griller and K. U. Ingold, Acc. Chem. Res. 13, 317-323 (1980).
34. (a) M. Newcomb and D. P. Curran, Acc. Chem. Res. 21, 206-215 (1988)
35. (b) J. M. Tanko and R. E. Drumright, J. Am. Chem. Soc. 112, 5362-5363 (1990).
36. T. Holm and I. Crossland, Acta Chem. Scand. 50, 90-93 (1996).
37. S. Yamago, S. Eajiri, M. Nakamura and E. Nakamura J. Am. Chem. Soc. 115, 5344-5345 (1993).
38. M. S. Alnajjar and H. G. Kuivila, J. Am. Chem. Soc. 107, 416-423 (1985).
39. A. Ohno, M. Goto, Y. Mikata, T. Kashiwagi and T. Maruyama, Bull. Chem. Soc. Jpn. 64, 87-90 (1991).
40. J.-M. Mattalia, B. Vacher, A. Samat and M. Chanon, J. Am. Chem. Soc. 114, 4111-4119 (1992).
41. S. Fukuzumi, M. Fujita, J. Otera and Y. Fujita, J. Am. Chem. Soc. 114, 10271-10278 (1992).
42. L. Eberson, New J. Chem. 16, 151-156 (1992).
43. S. Fukuzumi and Y. Tokuda, J. Phys. Chem. 96, 8409-8413 (1992).
44. (a) S. Fukuzumi, Adv. Electron Transfer 2, 67-175 (1992)
45. (b) J. W. Bunting, Bioorg. Chem. 19, 456-491 (1991)
46. (c) J. D. Wuest (Ed.), Tetrahedron Symposium-in-Print, Tetrahedron 42, 941-1116 (1986).
47. F. G. Bordwell and J. A. Harrelson, Jr, J. Org. Chem. 54, 4893-4898 (1989).
48. H. Lund, K. Daasbjerk, T. Lund, S. U. Pedersen, Acc. Chem. Res. 28, 313-319 (1995).
49. S. S. Shaik, Acta. Scand. 44, 205-221 (1990).
50. (a) C. J. Schlesener, C. Amatore and J. K. Kochi, J. Am. Chem. Soc. 106, 3567-3577 (1984)
51. (b) E. Baciocchi, M. Bietti and M. Mattioli, J. Org. Chem. 58, 7106-7110 (1993).
52. (a) S. Fukuzumi, S. Koumitsu, K. Hiaronaka and T. Tanaka, J. Am. Chem. Soc. 109, 305-316 (1987)
53. (b) S. Fukuzumi, N. Nishizawa and T. Tanaka, J. Org. Chem. 49, 3571-3578 (1984).
54. S. Fukuzumi, T. Kitano, M. Ishikawa and Y. Matsuda, Chem. Phys. 176, 337-347 (1993).
55. H. Mayr, N. Basso and G. Hagen, J. Am. Chem. Soc. 114, 3060-3066 (1992).
56. Y. Apeloig, O. Merin-Aharoni, D. Danovich, A. Ioffe and S. Shaik, Isr. J. Chem. 33, 387-402 (1993).
57. M. Fujita, S. Fukuzumi and J. Otera, J. Mol. Catal. 85, 143-148 (1993).
58. (a) J.-M. Savéant, Acc. Chem. Res. 26, 455-461 (1993)
59. (b) N. Kimura and S. Takamuku, Bull. Chem. Soc. Jpn 66, 3613-3617 (1993)
60. (c) J.-M. Savéant, J. Am. Chem. Soc. 114, 10595-10602 (1992)
61. (d) J. Bertran, I. Gallardo, M. Moreno and J.-M. Savéant, J. Am. Chem. Soc. 114, 9576-9583 (1992)
62. (e) C. P. Andrieux, A. Le Gorande and J.-M. Savéant, J. Am. Chem. Soc. 114, 6892-6904 (1992)
63. (f) J. Grimshaw, J. R. Langan and G. A. Salmon, J. Chem. Soc., Faraday Trans. 90, 75-81 (1994).
64. E. C. Ashby, X. Sun and J. L. Duff, J. Org. Chem. 59, 1270-1278 (1994).
65. K. Müllen, J. Alexander, K.-U. Klabunde, F-G. Klärner, H. Lund and T. Lund, Chem. Ber. 125, 505-513 (1992).
66. R. Subramanian, K. M. Kadish, M. N. Vijayashree, X. Gao, M. T. Jones, M. D. Miller and K. L. Krause, T. Suenobu and S. Fukuzumi, J. Phys. Chem. 100, 16327-16335 (1996).
67. N. Kimura and S. Takamuku, J. Am. Chem. Soc. 116, 4087-4088 (1994).
68. K. Daasbjerg, U. Pedersen and H. Lund, Acta Chem. Scand. 45, 424-430 (1991).
69. L. Eberson and S. S. Shaik, J. Am. Chem. Soc. 112, 4484-4489 (1990).
70. (a) G. N. Sastry and S. Shaik, J. Phys. Chem. 100, 12241-12252 (1996)
71. (b) K. Daasbjerg and T. B. Christensen, Acta Chem. Scand. 49, 128-132 (1995)
72. (c) J. J. Eisch, Res. Chem. Intermed. 22, 148-188 (1996).
73. (a) M. Chanon and M. L. Tobe, Angew. Chem., Int. Ed. Engl. 21, 1-23 (1982)
74. (b) N. L. Bauld, Tetrahedron 45, 5307-5363 (1989)
75. (c) N. Kornblum, Angew. Chem., Int. Ed. Engl. 14, 734-745 (1975)
76. (d) J. F. Bunnett, Acc. Chem. Res. 25, 2-9 (1992)
77. (e) W. R. Bowman, Photoinduced Electron Transfer, C 487-552 (1988)
78. (f) J. A. Orvik, J. Org. Chem. 61, 4933-4936 (1996).
79. R. B. Woodward, J. Am. Chem. Soc. 64, 3058-3059 (1942).
80. S. Fukuzumi and J. K. Kochi, Tetrahedron 38, 1035-1049 (1982).
81. M. Dern, H.-G. Korth, G. Kopp and R. Sustmann, Angew. Chem., Int. Ed. Eng., 24, 337 (1985).
82. S. Fukuzumi and T. Okamoto, J. Am. Chem. Soc. 115, 11600-11601 (1993).
83. (a) M. Schmittel and H. von Seggern, J. Am. Chem. Soc. 115, 2165-2177 (1993)
84. (b) M. Schmittel, C. Wöhrle and I. Bohn, Chem. Eur. J. 2, 1031-1040 (1996)
85. (c) T. Kim, R. J. Pye and N. L. Bauld, J. Am. Chem. Soc. 112, 6285-6290 (1990)
86. (d) L. Eberson and B. Olofson, Acta Chem. Scand. 45, 316 (1991).
87. M. Patz, H. Mayr, J. Maruta and S. Fukuzumi, Angew. Chem., Int. Ed. Engl. 34, 1225-1227 (1995).
88. M. Patz, K. Okubo, T. Suenobu, S. Itoh and S. Fukuzumi, 43rd Symposium on Organometallic Chemistry, Osaka, Japan, Abstract No. PA114 (1996).
89. (a) M. E. Niyazymbetov and D. H. Evans, J. Chem. Soc., Perkin Trans. 2 1333-1338 (1993)
90. (b) C. D. Ritchie, J. Am. Chem. Soc. 105, 7313-7318 (1983)
91. (c) M. E. Niyazymbetov, Z. Rongfeng and D. H. Evans, J. Chem. Soc., Perkin Trans. 2 1957-1961 (1996).
92. (a) J. K. Kochi, Adv. Phys. Org. Chem. 29, 185-272 (1994)
93. (b) E. K. Kim, T. M. Bookman and J. K. Kochi, J Am. Chem. Soc. 115, 3091-3104 (1993)
94. (c) E. Bosch and J. K. Kochi, J. Org. Chem. 59, 3314-3325 (1994)
95. (d) W. A. Pryor, G. J. Gleicher, J. P. Cosgrove and D. F. Church, J. Org. Chem. 49, 5189-5194 (1984)
96. (e) T. Keumi, K. Kamaka, H. Hasegawa, N. Minamide, Y. Inone and H. Kaitajima, Chem. Lett. 1285-1288 (1988)
97. (f) for a counter position, see L. Eberson, M. P. Hartschorn and F. Radner, Acta Chem. Scand. 48, 937-950 (1994).
98. (a) L. Eberson, M. P. Hartshorn, F. Radner and O. Persson, J. Chem. Soc., Chem. Commun. 215-216 (1996)
99. (b) S. M. Hibig, W. Jung and J. K. Kochi, J. Org. Chem. 59, 6233-6244 (1994).
100. (a) R. Bacaloglu, A. Blasko, C. A. Bunton, F. Ortega and C. Zucco, J. Am. Chem. Soc. 114, 7708-7718 (1992)
101. (b) D. P. Ip, C. D. Arthur, R. E. Winans and E. H. Appelman, J. Am. Chem. Soc. 103, 1964-1968 (1981).
102. J. Otera, Y. Fujita, N. Sakuta, M. Fujita and S. Fukuzumi, J. Org. Chem. 61, 2951-2962 (1996).
103. (a) M. Fujita, S. Fukuzumi, G. Matsubayashi and J. Otera, Bull Chem. Soc. Jpn. 69, 1107-1116 (1996)
104. (b) S. Fukuzumi, M. Fujita, G. Matsubayashi and J. Otera, Chem. Lett. 1451-1454 (1993).
105. S. Fukuzumi, Bull. Chem. Soc. Jpn 70, 1-28 (1997).
106. Takuwa, J. Shiigi and Y. Nishigaichi, Tetrahedron Lett. 34, 3457-3460 (1993)
107. (b) S. Fukuzumi, M. Fujita and J. Otera, J. Chem. Soc., Chem. Commun. 1536-1537 (1993)
108. (c) S. Fukuzumi, Y. Tokuda, T. Kitano, T. Okamoto and J. Otera, J. Am. Chem. Soc. 115, 8960-8968 (1993)
109. (d) A. Anne, J. Moiroux and J. M. Savéant, J. Am. Chem. Soc. 115, 10224-10230 (1993).
110. E. C. Ashby, Pure Appl. Chem. 52, 545 (1980).
111. (a) H. Yamataka, N. Miyano and T. Hanafusa, J. Org. Chem. 56, 2573-2575 (1991)
112. (b) H. Yamataka, T. Matsuyama and T. Hanafusa, J. Am. Chem. Soc. 111, 4912-4918 (1989).
113. N. S. Nudelman and F. Doctorovich, Tetrahedron 50, 4651-4666 (1994).
114. H. Yamataka, K. Nagareda, T. Takatsuka, K. Ando, T. Hanafusa and S. Nagase, J. Am. Chem. Soc. 115, 8570-8576 (1993).