Selective oxygen transfers with iron(III) porphyrin nitrite

Journal of Organic Chemistry

Volumn 61, Issue 18, 1996, Pages 6388-6395

  O'Shea, Stephen K ^a   Wang, Wen ^a   Wade, Ruth S ^a   Castro, Charles E ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001672904     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960546x     Document Type: Article

References (66)

1. McMurry, T. J.; Groves, J. T. Metalloporphyrin Models for Cytochrome P-450. In Cytochrome P-450; Plenum Press: New York, 1986; Chapter 1, pp 1-28.
2. (b) Groves, J. T.; Gross, Z. NATO ASI Ser., Ser. C 1995, 459 (Bioinorganic Chemistry) 39.
3. Groves, J. T.; Nemo, T. E.; Myers, R. S. J. Am. Chem. Soc. 1979, 101, 1032-1033.
4. (a) Groves, J. T.; Nemo, T. E. J. Am. Chem. Soc. 1983, 105, 5786-5791.
5. (b) Groves, J. T.; Myers, R. S. J. Am. Chem. Soc. 1983, 105, 5791-5796.
6. (c) Kodadek, T.; Raybuck, S. H.; Collman, J. P.; Brauman, J. I.; Papazian, L. 1985, 107, 4343-4345.
7. (d) Traylor, T. G.; Marsters, J. C., Jr.; Nakano, T.; Dunlap, B. E. J. Am. Chem. Soc. 1985, 107, 5537-5539.
8. (a) Groves, J. T.; Watanabe, Y. J. Am. Chem. Soc. 1986, 108, 507.
9. (b) Yamaguchi, K.; Watanabe, Y.; Morishima, I. J. Am. Chem. Soc. 1993, 115, 4058-4065.
10. (c) Machili, K.; Watanabe, Y.; Morishim, I. J. Am. Chem. Soc. 1995, 117, 6691-6697.
11. (a) He, G-X.; Bruice, T. C. J. Am. Chem, Soc. 1991, 113, 2743.
12. (b) Beck, M. J.; Gopinath, E.; Bruice, T. C. J. Am. Chem. Soc. 1993, 115, 21.
13. (c) Machii, K.; Watanabe, Y.; Morishima, I. J. Am. Chem. Soc. 1995, 117, 6691.
14. Nee, M. W.; Bruice, T. C. J. Am. Chem. Soc. 1982, 104, 6123.
15. Bernadou, J.; Fabiano, A.-S.; Robert, A.; Meunier, B. J. Am. Chem. Soc. 1994, 116, 9375.
16. (a) Collman, J. P.; Kodadek, T.; Raybuck S. A.; Meunier, B. Proc. Natl. Acad. Sci. U.S.A. 1983, 80, 7039.
17. (b) Meunier, B.; Guilmet, E.; DeCarvalho, M. E.; Poilblanc, R. J. Am. Chem. Soc. 1984, 106, 6668-6676.
18. Traylor, P. S.; Dolphin, D.; Traylor T. G. J. Chem. Soc., Chem. Commun. 1984, 279.
19. Castellano, A. J.; Bruice, T. C. J. Am. Chem. Soc. 1988, 116, 158.
20. (a) Arasasingham, R. D.; He, G.-X.; Bruice, T. C. J. Am. Chem. Soc. 1993, 115, 7955.
21. (b) Groves, J. T.; Ahn, K. H.; Quinn, R. J. Am. Chem. Soc. 1988, 110, 4217.
22. (c) Garrison, M. J.; Lee, R. W.; Bruice, T. C. Inorg. Chem. 1990, 29, 2019.
23. (d) Park, Y. C.; Na, H. G.; Kim, S. S. J. Korean Chem. Soc. 1995, 39, 364.
24. (e) Scharbert, B.; Zeisberger, E.; Paulus, E. J. Organomet. Chem. 1995, 155, 59.
25. (a) Traylor, T, G.; Hill, K. W.; Famm, W.-P. Tsuchuya, S.; Dunlap, B. E. J. Am. Chem. Soc. 1992, 114, 1308.
26. (b) Ohtake, H.; Higuchi, T.; Hirobe, M. J. Am. Chem. Soc. 1992, 114, 10660.
27. (a) Tomofumi, S.; Naoki, M.; Masaki, H. Chem. Pharm Bull. 1984, 32, 1252.
28. (b) Ando, W.; Tajima, R.; Takata, T. Tetrahedreon Lett. 1982, 23, 1685.
29. (a) Groves, J. T.; Watanabe, Y. J. Am Chem. Soc. 1986, 108, 507.
30. (b) Traylor, T. G.; Miksztal, A. R. J. Am. Chem. Soc. 1987, 109, 2770.
31. (c) Inchley, P.; Smith, J. R. L. J. Chem. Soc., Perkin Trans. 2 1995, 1579.
32. (a) Groves, J. T.; Gross, Z.; Stern, M. K. Inorg. Chem. 1994, 33, 5065.
33. (b) Yamaguchi, K.; Watanabe Y.; Morishima, I. J. Am. Chem. Soc. 1992, 114, 1721.
34. (c) Balch, A. L.; Cornman, C. R.; Latos-Gratzynski, L.; Renner, M. W. J. Am. Chem. Soc. 1992, 114, 2230.
35. (a) Mirafzal, G. A.; Kim, T., Liu. J.; Bauld, M. L. J. Am. Chem. Soc. 1992, 114, 10968.
36. (b) Kim, T., Mirafszal, G. A.; Liu. J.; Bauld, N. L. J. Am. Chem. Soc. 1993, 115, 7653.
37. (a) Nam, W.; Valentine, J. S. J. Am. Chem. Soc. 1993, 115, 1772.
38. (b) The Zn references.
39. Castro, C. E.; Bartnicki, E. W. J. Org. Chem. 1994, 59, 4051.
40. Wade, R. S.; Castro, C. E. Chem. Res. Toxicol. 1990, 3, 289.
41. (a) Castro, C. E.; O'Shea, S. K. J. Org. Chem. 1995, 60, 1922.
42. (b) Castro, C. E. J. Am. Chem. Soc. 1996, 118, 3984.
43. A nitrogen rather than oxygen label was selected because the former can give an all or nothing result, and it is subject to both MS and NMR analysis.
44. Schwartz, E.; White, W. H. Trace Atmospheric Constituents, Properties, Transformation and Fates; John Wiley and Sons: New York, 1983; pp 1-117.
45. Kontrakis, P.; Wolfson, J. M.; Bunyaviroch, A.; Fruehlich, S. E.; Hirono, K.; Mulik, J. D. Anal. Chem. 1993, 65, 209.
46. March, J. B. Advanced Organic Chemistry, 3rd ed.; John Wiley and Sons: New York, 1985; pp 1066 ff.
47. An allylic C-H abstraction followed by HO return to the terminal carbon.
48. Belser, N. O.; Castro, C. E. J. Agric. Food Chem. 1971, 12, 22.
49. (a) Sharma, V. S.; Traylor, T. G.; Gardiner, G. R.; Mizuka, H. Biochemistry 1987, 26, 3837.
50. (b) Gibson, Q, H. et al. J. Biol. Chem. 1991, 226, 13097.
51. (c) Petrich, J. W. et al. Biochemistry 1991, 30, 2975.
52. (d) Hishino, M. et al. J. Am. Chem. Soc. 1993, 115, 9568.
53. Atkinson, R. et al. Supplement 4. J. Phys. Chem. Ref. Data 1992, 21, 1125.
54. Wink, D. A.; Darbyshire, J. F.; Nims, R. W.; Saavedva, J. E.; Ford, P. C. Chem. Res. Toxicol. 1993, 6, 23.
55. White, K. A.; Marietta, M. A. Biochemistry 1992, 31, 6627.
56. Elsayed, N. M., Ed. Effects of Exposure to Nitrogen Dioxide. Toxicology 1994, 89, 161.
57. (a) Nasri, H.; Goodwin, J. A.; Scheidt, W. R. Inorg. Chem. 1990, 29, 185.
58. (b) Nasri, H.; Haller, K. J.; Wang, Y.; Huynh, B. H.; Scheidy, W. R. Inorg. Chem. 1992, 31, 3459.
59. (a) Solar, J. P.; Mares, F.; Diamond, S. E. Catal. Rev. 1985, 27, 1.
60. (b) Andrews, M. A.; Chang, T.-C-T.; Cheng, C. W.-F. Organometallics 1985, 4, 268.
61. (c) Leising, R. A.; Takeuchi, K. J. Am. Chem. Soc, 1988, 110, 4079.
62. (d) Ercolani, C.; Pavletti, A.; Pennesi, G.; Rossi, G. J. Chem. Soc., Dalton Trans. 1991, 1317.
63. Castro, C. E.; Wade, R. S.; Riebeth, D. M.; Bartnicki, E. W.; Belser, N. O. Environ. Toxicol. Chem. 1992, 11, 757.
64. Chow, T. J.; Johnstone, M. S. Anal. Chim. Acta 1962, 27, 441.
65. Castro, C. E.; Robertson, C.; Davis, H. Biorg. Chem. 1974, 3, 343.
66. CRC Handbook of Chemistry and Physics; Lide, D. R., Ed.; CRC: Boston, 1990; Vol. 9, p 96.