A comparative mechanistic study of the oxidation of phenols in aqueous solution by oxomanganese(IV) and oxoiron(IV) 5,10,15,20-tetrakis(2-N- methylpyridyl) porphyrin

Journal of Molecular Catalysis A: Chemical

Volumn 113, Issue 1-2, 1996, Pages 131-145

  Kamp, Norbert W J ^a   Lindsay Smith, John R ^b  

^a UNIVERSITY OF BONN   (Germany)

^b UNIVERSITY OF YORK   (United Kingdom)

Author keywords

Hammett equations; Iron; Manganese; Monopersulphate; Oxidation; Oxo complexes; Peroxidase; Phenol; Porphyrin

Indexed keywords

EID: 0030602072     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1381-1169(96)00057-X     Document Type: Article

References (42)

1. [1] (a) P.R. Ortiz de Montellano (Ed.), Cytochrome P450: Structure, Mechanism and Biochemistry, Plenum, New York, 1986;
2. (b) H.B. Dunford, in J. Everse, K.E. Everse and M.B. Grisham (Ed.), Peroxidases in Chemistry and Biology, Vol. 2, CRC Press, Boca Raton, FL, 1991, p. 1;
3. (c) P.R. Ortiz de Montellano, Ann. Rev. Pharmacol, Toxicol., 32 (1992) 89.
4. [2] (a) B. Meunier, Chem. Rev., 92 (1992) 1411;
5. (b) F. Montanari and L. Casella (Ed.), Metalloporphyrin Catalysed Oxidations, Kluwer, Dordrecht, 1994;
6. (c) R.A. Sheldon (Ed.) Metalloporphyrins in Catalytic Oxidations, Marcel Dekker, New York, 1994.
7. [3] M.H. Gelb, W.A. Toscano and S.G. Sugar, Proc. Natl. Acad. Sci. USA, 79 (1982) 5758.
8. [4] (a) R. Makino, T. Uno, Y. Nishimura, T. Iizuka, M. Tsuboi and Y. Ishimura, J. Biol. Chem., 261 (1986) 8376;
9. (b) H. Hori, M. Ikeda and T. Yonetani, Biochim, Biophys. Acta, 912 (1987) 74;
10. (c) R.J. Nick, G.B. Ray, K.M. Fish, T.G. Spiro and T.J. Groves, J. Am. Chem. Soc., 113 (1991) 1838.
11. [5] (a) C.L. Hill and B.C. Schardt, J. Am. Chem. Soc. 102 (1980) 6374;
12. (b) J.T. Groves, W.J. Kruper and R.C. Haushalter, J. Am. Chem. Soc., 102 (1980) 6375;
13. (c) E. Guilmet and B. Meunier, Tetrahedron Lett., (1980) 4449;
14. (d) S. Campestrini and B. Meunier, Inorg. Chem., 31, (1992) 1999;
15. (e) J.P. Collman, X. Zhang, R.T. Hembre and J.I. Brauman, J. Am. Chem. Soc., 112 (1992) 5325;
16. (f) F. Montanari, S. Banfi, G. Pozzi and S. Quici, in F. Montanari and L. Casella (Ed.), Metalloporphyrin Catalysed Oxidations, Kluwer, Dordrecht, 1994, p. 149.
17. [6] (a) I. Tabushi and N. Koga, J. Am. Chem. Soc., 101 (1979) 6456;
18. (b) D. Mansuy, M. Fontecave and J.F. Bartoli, J. Chem. Soc. Chem. Commun., (1983) 253;
19. (c) E.I. Karasevich, A.M. Khenkin and A.E. Shilov, J. Chem. Soc., Chem. Commun., (1987) 731;
20. (d) P. Battioni, J.F. Bartoli, P. Leduc, M. Fontecave and D. Mansuy, J. Chem. Soc. Chem. Commun., (1987) 791;
21. (e) P. Battioni, J.P. Renaud, J.F. Bartoli, M. Reina-Artilles, M. Fort and D. Mansuy, J. Am. Chem. Soc., 110 (1988) 8462;
22. (f) A.E. Shilov and E.I. Karasevich, in F. Montanari and L. Casella (Ed.), Metalloporphyrin Catalysed Oxidations, Kluwer, Dordrecht, 1994, p. 87.
23. [7] (a) J.T. Groves and M.K. Stern, J. Am. Chem. Soc., 109 (1987) 3821;
24. (b) R.D. Arasasingham, G. He, T.C. Bruice, J. Am. Chem. Soc. 115 (1993) 7985.
25. [8] N. Colclough and J.R. Lindsay Smith, J. Chem. Soc. Perkin Trans. 2, (1994) 1139.
26. [9] M. Vidal, M. Bonnafous; S. Defrance, P. Loiseau, J. Bernadou and B. Meunier, Drug Metab. Dispos. 21 (1993) 811.
27. [10] L.O. Spreer, A. Leone, A.C. Maliyackel, J.W. Otvos and M. Calvin, Inorg. Chem. 27 (1988) 2401.
28. [11] N. Carnieri, A. Harriman and G. Porter, J. Chem. Soc., Dalton Trans., (1982) 931.
29. [12] E.P. Serjeant and B. Dempsey, Ionisation Constants of Organic Acids in Aqueous Solution, Pergamon Press, Oxford, 1979.
30. [13] D.H. Mc Daniel and H.C. Brown, J. Org. Chem. 23 (1958) 420.
31. [14] H.C. Brown and Y. Okamoto, J. Am. Chem. Soc. 80 (1958) 4979.
32. [15] (a) J.M. Dust and D.R. Arnold, J. Am. Chem. Soc. 105 (1983) 1221 and 6531;
33. (b) D.D.M. Wayne and D.R. Arnold, Can. J. Chem. 62 (1984) 1164;
34. (c) D.R. Arnold in H.G. Viehe, Z. Janousek and R. Merenyi (Ed.), Substituent Effects in Radical Chemistry, Riedel, Dordrecht, 1986, p. 171.
35. [16] G. Galliani and B. Rindone, J. Chem. Soc., Perkin. Trans. II, (1976) 1803.
36. [17] J.T. Groves and D.V. Subramanian, J. Am. Chem. Soc., 106 (1984) 2177.
37. [18] A.D. Adler, J. Org. Chem., 32 (1967) 476.
38. [19] K. Kalyanasundaram, Inorg. Chem., 23 (1984) 2453.
39. [20] P. Hambright, T. Gore and M. Burton, Inorg. Chem., 15 (1976) 2314.
40. [21] P. Hambright, A. Adeyemo, A. Shamim and S. Lemelle, Inorg. Synth., 23 (1985) 56.
41. [22] R.F. Pasternack, P.R. Huber, P. Boyd, G. Engasser, L. Francesconi, E. Gibbs, P. Fasella, G.C. Venture and L. de C. Hinds, J. Am. Chem. Soc., 13 (1972) 4511Maltrese cross signMaltrese cross sign.
42. [23] O. Herrmann, S. Husain Mehdi, A. Corsini, Can. J. Chem., 56 (1978) 1084.