Hydroxylation of aliphatic hydrocarbons with m-chloroperbenzoic acid catalyzed by electron-deficient iron(III) porphyrin complexes

Bulletin of the Chemical Society of Japan

Volumn 72, Issue 4, 1999, Pages 707-713

  Lim, Mi Hee ^a   Lee, Yoon Jung ^a   Goh, Yeong Mee ^a   Nam, Wonwoo ^a   Kim, Cheal ^b  

^a Ewha Womans University   (South Korea)

^b Seoul National University of Science and Technology   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOIC ACID DERIVATIVE; HYDROCARBON; PORPHYRIN; WATER;

ARTICLE; CATALYSIS; CHEMICAL REACTION; HYDROXYLATION; KINETICS; PROTEIN STRUCTURE; SYNTHESIS;

EID: 0032910838     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.72.707     Document Type: Article

References (65)

1. a) M. Sono, M. P. Roach, E. D. Coulter, and J. H. Dawson, Chem. Rev., 96, 2841 (1996);
2. b) P. R. Ortiz de Montellano, "Cytochrome P-450: Structure, Mechanism, and Biochemistry," Plenum Press, New York (1986).
3. a) Y. Watanabe, in "Oxygenases and Model Systems," ed by T. Funabiki, Kluwer Academic Publishers, Dordrecht (1997), p. 223;
4. b) T. G. Traylor and P. S. Traylor, in "Active Oxygen in Biochemistry," ed by J. S. Valentine, C. S. Foote, A. Greenberg, and J. F. Liebman, Blackie Academic & Professional, Chapman & Hall, London (1995), p. 84;
5. c) F. Montanari and L. Casella, "Metalloporphyrins Catalyzed Oxidations," Kluwer Academic Publishers, Dordrecht (1994);
6. d) R. A. Sheldon, "Metalloporphyrins in Catalytic Oxidations," Marcel Dekker, Inc., New York (1994);
7. e) D. Mansuy, Coord. Chem. Rev., 125, 129 (1993);
8. f) B. Meunier, Chem. Rev., 92, 1411 (1992).
9. a) J. T. Groves, T. E. Nemo, and R. S. Myers, J. Am. Chem. Soc., 101, 1032 (1979);
10. b) J. T. Groves and T. E. Nemo, J. Am. Chem. Soc., 105, 6243 (1983).
11. a) D. Dolphin, T. G. Traylor, and L. Y. Xie, Acc. Chem. Res., 30, 251 (1997);
12. b) Y. J. Lee, Y. M. Goh, S.-Y. Han, C. Kim, and W. Nam, Chem. Lett., 1998, 837;
13. c) T. Nakano, N. Agatsuma, S. Kodama, H. Kakuda, and D. Dolphin, Bull. Chem. Soc. Jpn., 69, 3513 (1996);
14. d) T. G. Traylor, C. Kim, J. L. Richards, F. Xu, and C. L. Perrin, J. Am. Chem. Soc., 117, 3468 (1995);
15. e) T. G. Traylor and S. Tsuchiya, Inorg. Chem., 26, 1338 (1987);
16. f) P. S. Traylor, D. Dolphin, and T. G. Traylor, J. Chem. Soc., Chem. Commun., 1984, 279;
17. g) C. K. Chang and F. Ebina, J. Chem. Soc., Chem. Commun., 1981, 778.
18. a) M. W. Grinstaff, M. G. Hill, J. A. Labinger, and H. B. Gray, Science, 264, 1311 (1994);
19. b) H. L. Chen, P. E. Ellis, Jr., T. Wijesekera, T. E. Hagan, S. E. Groh, J. E. Lyons, and D. P. Ridge, J. Am. Chem. Soc., 116, 1086 (1994);
20. c) P. E. Ellis, Jr., and J. E. Lyons, Coord. Chem. Rev., 105, 181 (1990);
21. d) S. Tsuchiya and M. Seno, Chem. Lett., 1989, 263.
22. a) J. F. Bartoli, P. Battioni, W. R. De Foor, and D. Mansuy, J. Chem. Soc., Chem. Commun., 1994, 23.
23. b) J. F. Bartoli, O. Brigaud, P. Battioni, and D. Mansuy, J. Chem. Soc., Chem. Commun., 1991, 440.
24. a) J. T. Groves, R. C. Haushalter, M. Nakamura, T. E. Nemo, and B. J. Evans, J. Am. Chem. Soc., 103, 2884 (1981);
25. b) H. Fujii, Chem. Lett., 1994, 1491;
26. c) H. Fujii, J. Am. Chem. Soc., 115, 4641 (1993);
27. d) D. Mandon, R. Weiss, K. Jayaraj, A. Gold, J. Terner, E. Bill, and A. X. Trautwein, Inorg. Chem., 31, 4404 (1992).
28. a) K. Yamaguchi, Y. Watanabe, and I. Morishima, J. Am. Chem. Soc., 115, 4058 (1993);
29. b) T. Higuchi, K. Shimada, N. Maruyama, and M. Hirobe, J. Am. Chem. Soc., 115, 7551 (1993);
30. c) Y. Watanabe, K. Yamaguchi, I. Morishima, K. Takehira, M. Shimizu, T. Hayakawa, and H. Orita, Inorg. Chem., 30, 2581 (1991);
31. d) J. T. Groves and Y. Watanabe, J. Am. Chem. Soc., 110, 8443 (1988);
32. e) W. A. Lee and T. C. Bruice, J. Am. Chem. Soc., 107, 513 (1985);
33. f) T. G. Traylor, W. A. Lee, and D. V. Stynes, J. Am. Chem. Soc., 106, 755 (1984).
34. R. D. Mair and A. J. Graupner, Anal. Chem., 36, 194 (1964).
35. T. La, G. M. Miskelly, and R. Bau, Inorg. Chem., 36, 5321 (1997)
36. A. Nanthakumar and H. M. Goff, J. Am. Chem. Soc., 112, 4047 (1990).
37. M. A. Phillippi and H. M. Goff, J. Am. Chem. Soc., 104, 6026 (1982).
38. a) C. Kim, K. Chen, J. Kim, and L. Que, Jr., J. Am. Chem. Soc., 119, 5964 (1997);
39. b) W. Nam, Y. M. Goh, Y. J. Lee, M. H. Lim, and C. Kim, Inorg. Chem., submitted for publication;
40. c) R. Mello, M. Fiorentino, C. Fusco, and R. Curci, J. Am. Chem. Soc., 111, 6749 (1989).
41. T. G. Traylor, K. W. Hill, W.-P. Fann, S. Tsuchiya, and B. E. Dunlap, J. Am. Chem. Soc., 114, 1308 (1992).
42. 17) then the ratio of the exo-lendo-norbornanol products is determined by the accessibility of the iron porphyrin complexes to the norbornane substrate.
43. J. T. Groves, J. Chem. Educ., 62, 928 (1985).
44. S.-Y. Choi, P. E. Eaton, P. F. Hollenberg, K. E. Liu, S. J. Lippard, M. Newcomb, D. A. Putt, S. P. Upadhyaya, and Y. Xiong, J. Am. Chem. Soc., 118, 6547 (1996).
45. a) P. Battioni, J. P. Renaud, J. F. Bartoli, M. Reina-Artiles, M. Fort, and D. Mansuy, J. Am. Chem. Soc., 110, 8462 (1988);
46. b) B. R. Cook, T. J. Reinert, and K. S. Suslick, J. Am. Chem. Soc., 108, 7281 (1986);
47. c) M. J. Nappa and C. A. Tolman, Inorg. Chem., 24, 4711 (1985).
48. a) W. Nam and J. S. Valentine, J. Am. Chem. Soc., 115, 1772 (1993);
49. b) J. Bernadou, A.-S. Fabiano, A. Robert, and B. Meunier, J. Am. Chem. Soc., 116, 9375 (1994);
50. c) M. Pitie, J. Bernadou, and B. Meunier, J. Am. Chem. Soc., 117, 2935 (1995);
51. d) R. Song, A. Sorokin, J. Bernadou, and B. Meunier, J. Org. Chem., 62, 673 (1997);
52. e) J. Bernadou and B. Meunier, J. Chem. Soc., Chem. Commun., 1998, 2167.
53. a) K. A. Lee and W. Nam, J. Am. Chem. Soc., 119, 1916 (1997);
54. b) J. T. Groves, J. Lee, and S. S. Maria, J. Am. Chem. Soc., 119, 6269 (1997).
55. Y. M. Goh and W. Nam, Inorg. Chem., submitted for publication.
56. 18O into the alcohol products. This is the effect of the electronic nature of iron porphyrin complexes on the rate of oxygen exchange between a high-valent iron oxo intermediate and labeled water (Scheme 1, pathway B). However, we do not have any results to explain the electronic effect of iron porphyrins on the oxygen exchange rate at this moment.
57. 18O is presumed to depend on the reaction temperature as well. However, we do not have any results to interpret such an effect at this moment.
58. a) W. M. Atkins and S. G. Sligar, J. Am. Chem. Soc., 109, 3754 (1987);
59. b) J. P. Jones and W. F. Trager, J. Am. Chem. Soc., 109, 2171 (1987);
60. c) P. Hoffmann, A. Robert, B. Meunier, Bull. Soc. Chim. Fr., 129, 85 (1992).
61. A. Sorokin, A. Robert, and B. Meunier, J. Am. Chem. Soc., 115, 7293 (1993).
62. A. B. Sorokin and A. M. Khenkin, J. Chem. Soc., Chem. Commun., 1990, 45.
63. A. Robert and B. Meunier, New J. Chem., 12, 885 (1988).
64. a) G. Brunton, D. Griller, L. R. Barclay, and K. U. Ingold, J. Am. Chem. Soc., 98, 6803 (1976);
65. b) H. Kwart, Acc. Chem. Res., 15, 401 (1982).