Water-Soluble Iron Porphyrin Complex-Catalyzed Epoxidation of Olefins with Hydrogen Peroxide and tert-Butyl Hydroperoxide in Aqueous Solution

Inorganic Chemistry

Volumn 37, Issue 4, 1998, Pages 606-607

  Yang, Sook Jung ^a   Nam, Wonwoo ^a  

^a Ewha Womans University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001125179     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic9710519     Document Type: Article

References (38)

1. (a) Traylor, T. G.: Traylor, P. S. In Active Oxygen in Biochemistry; Valentine, J. S., Foote, C. S., Greenberg, A., Liebman, J. F., Eds.; Blackie Academic & Professional, Chapman & Hall: London, 1995; pp 84-187.
2. (b) Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841-2887.
3. (c) Meunier, B. Chem. Rev. 1992, 92, 1411-1456.
4. Traylor, T. G.; Kim, C.; Richards, J. L.; Xu, F.; Perrin, C. L. J. Am. Chem. Soc. 1995, 117, 3468-3474 and references therein.
5. Lee, Y. J.; Goh, Y. M.; Kim, C.; Nam, W. Inorg. Chem., submitted for publication.
6. (a) Panicucci, R.; Bruice, T. C. J. Am. Chem. Soc. 1990, 112, 6063-6071.
7. (b) Balasubramanian, P. N.; Lee, R. W.; Bruice, T. C. J. Am. Chem. Soc. 1989, 111, 8714-8721.
8. (a) Almarasson, O.; Bruice, T. C. J. Am. Chem. Soc. 1995, 111, 4533-4544 and references therein,
9. (b) Arasasingham, R. D.; Bruice, T. C. In The Activation of Dioxygen and Homogeneous Catalytic Oxidation; Barton, D. H. R., Martell, A. E., Sawyer, D. T., Eds.; Plenum Press: New York, 1993; pp 147-169.
10. (c) Bruice, T. C. Ace. Chem. Res. 1991, 24, 243-249.
11. Bernadou, J.; Fabiano, A.-S.; Robert, A.; Meunier, B. J. Am. Chem. Soc. 1994, 116, 9375-9376.
12. Groves, J. T.; Lee, J.; Maria, S. S. J. Am. Chem. Soc. 1997, 779, 6269-6273.
13. Fe(TDCPPS) was obtained from Mid-Century Chemical.
14. 6
15. 4 might be due to the reactions being studied at pH 7.0 (see Figure 1).
16. (a) Song, R.; Sorokin, A.; Bernadou, J.; Meunier, B. J. Org. Chem. 1997, 62, 673-678.
17. (b) Labat, G.; Meunier, B. J. Org. Chem. 1989, 54, 5008-5011.
18. (c) Labat, G.; Meunier, B. New J. Chem. 1989, 13, 801-804.
19. Deoxygenated water was prepared by three freeze-pump-thaw cycles, and the epoxidation reaction was performed under an argon atmosphere.
20. 5 should be investigated at the same pH.
21. 5 solutions in water and 0.1 M MCPBA solution in methanol) was added to a reaction solution containing Fe(TDCPPS) (0.04 mM) and cis-stilbene (1 mM) in buffered solution. The reaction mixture was stirred for 30 min at 25 °C and then analyzed by HPLC. Products were separated on a Waters Symmetry C18 column, 5 μM, eluted by a mixture of methanol/water, 80:20 (v/v), and detection was made at 215 or 254 nm.
22. 5 were 75, 63, 81, and 69% based on the substrate consumed, respectively, and the yields of trans-stilbene oxide were less than 2% in all the reactions.
23. (a) Groves, J. T.; Gross, Z.; Stern, M. K. Inorg. Chem. 1994, 33, 5065-5072.
24. (b) He, G.-X.; Bruice, T. C. J. Am. Chem. Soc. 1991, 113, 2747-2753.
25. (c) Labeque, R.; Marnett, L. J. J. Am. Chem. Soc. 1989, 111, 6621-6627.
26. (d) Yamamoto, T.; Kimura, M. J. Chem. Soc., Chem. Commun. 1977, 948-949.
27. (a) Robert, A.; Meunier, B. New J. Chem. 1988, 72, 885-896.
28. (b) Thompson, R. C.; Wieland, P.; Appelman, E. H. Inorg. Chem. 1979, 18, 1974-1977.
29. Lee, K. A.; Nam. W. J. Am. Chem. Soc. 1997, 119, 1916-1922.
30. 5 in aqueous solution has also been observed; however, no clear explanation has been provided for such a phenomenon. See ref 11.
31. Groves, J. T.; Watanabe, Y. J. Am. Chem. Soc. 1988, 110, 8443-8452.
32. (a) Aikens, J.; Sligar, S. G. J. Am. Chem. Soc. 1994, 116, 1143-1144.
33. (b) Gerber, N. C.; Sligar, S. G. J. Am. Chem. Soc. 1992, 114, 8742-8743.
34. (c) Traylor, T. G.; Ciccone, J. P. J. Am. Chem. Soc. 1989, 111, 8413-8420.
35. (d) Traylor, T. G.; Lee, W. A.; Stynes, D. V. J. Am. Chem. Soc. 1984, 106, 755-764.
36. 23
37. (a) Arasasingham, R. D.; Jeon, S.; Bruice, T. C. J. Am. Chem. Soc. 1992, 114, 2536-2544.
38. (b) Allentoff, A. J.; Bolton, J. L.; Wilks, A.; Thompson, J. A.; Ortiz de Montellano, P. R. J. Am. Chem. Soc. 1992, 114, 9744-9749.