The oxidation of ethylbenzene and other alkylaromatics by dioxygen catalysed by iron(III) tetrakis(pentafluorophenyl)porphyrin and related iron porphyrins

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 7, 2000, Pages 1541-1551

  Evans, Steven ^a   Smith, John R Lindsay ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYST ACTIVITY; COMPOSITION EFFECTS; DEGRADATION; FREE RADICAL REACTIONS; IRON COMPOUNDS; OXIDATION; REACTION KINETICS; THERMAL EFFECTS;

ALKYLAROMATICS; CATALYST DEGRADATION; ETHYLBENZENE; IRON TETRAKISPENTAFLUOROPHENYLPORPHYRIN; RADICAL AUTOOXIDATION MECHANISM; TIME DEPENDENCE;

AROMATIC COMPOUNDS;

EID: 0034236759     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/b000967i     Document Type: Article

References (66)

1. R. A. Sheldon, Chemtech, 1991, 566.
2. R. A. Sheldon, J. Chem. Technol. Biotechnol., 1997, 68, 381.
3. (a) A. L. Feig, and S. J. Lippard, Chem. Rev., 1994, 94, 759
4. (b) A. L. Feig, and S. J. Lippard, Active oxygen in biochemistry, eds. J. S. Valentine, C. S. Foote, A. Greenberg and J. F. Liebman, Chapman and Hall, London, 1995
5. (c) A. L. Feig and S. J. Lippard, Cytochrome P450: structure, mechanism and biochemistry, ed. P. R. Ortiz de Montellano, Plenum, New York, 2nd Edn., 1995
6. (d) L. Que and R. Y. N. Ho, Chem. Rev., 1996, 96. 2607
7. (e) B. J. Wallar, and J. D. Lipscomb, Chem. Rev., 1996, 96, 2625
8. (f) R. A. Sheldon, Catalytic activation and functionalisation of light alkanes, Kluwer Academic, Dordrecht, 1998, p. 259
9. (g) A. E. Shilov and A. A. Steinman, Acc. Chem. Res., 1999, 32, 763.
10. (a) B. Meunier, Chem. Rev., 1992, 92, 1411
11. (b) D. Mansuy, Coord. Chem. Rev., 1993, 125, 129
12. (a) P. E. Ellis and J. E. Lyons, J. Chem. Soc., Chem. Commun. 1989, 1315
13. (b) J. E. Lyons, Coord. Chem. Rev., 1990, 105, 181
14. (c) J. E. Lyons, P. E. Ellis and V. A. Durante, Stud. Surf. Sci. Catal., 1991, 67, 99
15. (d) J. E. Lyons, P. E. Ellis, H. K. Myers and R. W. Wagner, J. Catal., 1993, 141, 311
16. (e) H. L. Chen, P. E. Ellis, T. Wijesekera, T. E., Hagan, S. E., Groh, J. E. Lyons and D. P. Ridge, J. Am. Chem. Soc., 1994, 116, 1086
17. (f) J. E. Lyons, P. E. Ellis and H. K. Myers, J. Catal., 1995, 155, 59.
18. (a) J. A. Labinger, Catal. Lett., 1994, 24, 95
19. (b) M. W. Grinstaff, M. G. Hill, J. A. Labinger and H. B. Gray, Science, 1994, 264, 1311
20. (c) E. R. Birnbaum, M. W. Grinstaff, J. A. Labinger, J. E. Bercaw, and H. B. Gray, J. Mol. Catal. A: Chem., 1995, 104, 119
21. (d) E. R. Birnbaum, M. W. Grinstaff, W. P. Schaeffer, J. A. Labinger, M. G. Hill and H. B. Gray, Inorg. Chem., 1995, 34, 4896
22. (e) A. Bottcher, E. A. Birnbaum, M. W. Day, H. B. Gray, M. W. Grinstaff and J. A. Labinger, J. Mol. Catal. A: Chem., 1997, 117, 229.
23. P. Battioni, J. F. Bartolli, D. Mansuy, Y. S. Byun and T. G. Traylor, J. Chem. Soc., Chem. Commun. 1991, 1051.
24. A. G. Rowley, in Organophosphorus Reagent in Organic Chemistry, ed. J. I. G. Cadogan, Academic Press, London, 1979, ch. 7
25. R. K. Jensen, S. Korcek, L. R. Mahoney and M. Zimbo, J. Am. Chem. Soc. 1979, 101, 7574.
26. M. Hofmann, Chem. Ber., 1962, 95, 528.
27. D. Gal, E. Danoczy and L. Paal-Lukacs, Ber. Bunsenges, Phys. Chem. 1993, 97, 554.
28. S. E. Caldwell and N. A. Porter, J. Am. Chem. Soc., 1995, 117, 8676.
29. S. E. Bell, P. R. Cooke, P. Inchley, D. R. Leonord, J. R. Lindsay Smith and A. Robbins, J. Chem. Soc., Perkin Trans, 2, 1991, 549.
30. P. R. Cooke, C. Gilmartin, G. W. Gray and J. R. Lindsay Smith, J. Chem. Soc., Perkin Trans. 2, 1995, 1573.
31. R. D. Arasingham, A. L. Balch, C. R. Cornman and L. Latos-Grazynski, J. Am. Chem. Soc., 1989, 111, 4357.
32. M. D'A. Antonio, R. Gonsalves, R. A. Johnstone, M. M. Pereira, J. Shaw and N. Sobral, Tetrahedron, Lett., 1991, 32, 187.
33. C. Walling, Free Radicals in Solution, J. Wiley, New York, 1957 ch. 9.
34. G. A. Russell, J. Am. Chem. Soc., 1957, 79, 3871.
35. (a) K. Adamic, J. A. Howard and K. U. Ingold, Can. J. Chem., 1969, 47, 3803
36. (b) L. A. Tavadyan, A. B. Nalbandyan, T. Vidoczyy and D. Gal, Oxid. Commun., 1983, 4, 189.
37. (c) T. J. Wallington, P. Dagaut and M. J. Kurylo, Chem. Rev., 1992, 92, 667.
38. R. D. Arasasingham, C. R. Cornman and A. L. Balch, J. Am. Chem. Soc., 1989, 111, 7800.
39. J. E. Bennett and R. Summers, Can. J. Chem., 1974, 52, 1377.
40. J. E. Bennett, G. Brunton, J. R. Lindsay Smith, T. M. F. Salmon and D.J. Waddington, J. Chem. Soc., Faraday Trans., 1987, 83, 2433
41. A. R. Costello, J. R. Lindsay Smith and D. J. Waddington, Int. J. Chem. Kinet., 1996, 28, 201.
42. J. A. Howard, J. E. Bennett and G. Brunton, Can. J. Chem., 1981, 59, 2253.
43. A. Factor, C. A. Russell and T. G. Traylor, J. Am. Chem. Soc., 1965, 87, 3692.
44. J. Fossey, D. Lefort and J. Sorba, Free Radicals in Organic Chemistry, J. Wiley, Chichester, 1995, p. 122.
45. (a) P. W. Atkins, Physical Chemistry, 4th Edition, Oxford University Press, oxford,, 1990, p. 670
46. (b) N. A. Porter, K. A. Mills, S. E. Calderwell and G. R. Dubay, J. Am. Chem. Soc., 1994, 116, 6697
47. C. D. Clark and M. Z. Hoffman, J. Phys. Chem., 1996, 100, 6697.
48. E. T. Denisov, Liquid Phase Reaction Rate Constants, Plenum Press, London, 1974 ch. 7
49. J. A. Howard and J. C. Scaiano, in Landolt-Bornstein New Series Volume 13: Radical Reaction Rates in Liquids. Subvolume d: Oxyl, Peroxyl and Related Radicals, Springer-Verlag, Berlin, 1984, Section 8.5.2.
50. E. R. Birnbaum, J. A. Labinger, J. E. Bercaw and H. B. Gray, Inorg. Chem., 1995, 34, 3625.
51. T. Wijesekera, A. Matsumoto, D. Dolphin and D. Lexa, Angew. Chem., Int. Ed. Engl., 1990, 29, 1028.
52. Handbook of Chemistry and Physics, 76th edition, ed. D. R. Lide, CRC Press, London, 1995, 8.43-8.55
53. Handbook of Chemistry and Physics, 76th Edition, ed. D. R. Lide, CRC Press, London, 1995, 9.15-9.73
54. K. A. Gardner, L. L. Kuehnert and J. M. Mayer, Inorg. Chem., 1997, 36, 2069.
55. P. A. MacFaul, I. W. C. E. Arends, K. U. Ingold and D. D. M. Wayner, J. Chem. Soc., Perkin Trans. 2, 1997, 135.
56. C. E. Boozer, B. W. Ponder, J. C. Trisler and C. E. Wightman, J. Am. Chem. Soc., 1956, 78, 1506.
57. D. Bouy-Debec, O. Brigaud, P. Leduc, P. Battioni and D. Mansuy, Gazz. Chim. Ital., 1996, 126, 8364.
58. F. Vogel, Textbook of Practical Organic Chemistry, 5th edition, eds. B. S. Furniss, A. J. Hannaford, P. W. G. Smith and A. R. Tatchell, J. Wiley, New York, 1989, p. 430.
59. H. Volz and S. Schneckenburger, J. Prakt. Chem., 1993, 335, 283.
60. C. Gilmartin, D. Phil. Thesis, University of York, York, UK, 1994
61. A. Jayaraj, A. Gold, G. E. Toney, J. H. Helms and W. E. Hatfield Inorg. Chem.,, 1986, 25, 3516.
62. G. Gray, D.Phil. Thesis, University of York, York, UK, 1998
63. J. S. Lindsey and R. W. Wagner, J. Org. Chem., 1989, 54, 828
64. D. R. Leanord, D.Phil. Thesis, University of York, York, UK, 1990.
65. M. Zipplies, W. A. Lee and T. C. Bruice, J. Am. Chem. Soc., 1986, 108, 4433.
66. T. La, R. Richards and G. M. Miskelly, Inorg. Chem., 1994, 33, 3159.