Kinetics of the reaction of mer-tris(picolinato) iron(III) with hydrogen peroxide in pyridine: Role of hydroxyl radicals in subsequent catalytic oxygenation of cyclohexane to the ketone

Inorganic Reaction Mechanisms

Volumn 6, Issue 3, 2007, Pages 169-183

  Richens, David T ^a   Jain, Sneh L ^a   Gale, Andrew C ^a  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

Cyclohexane oxygenation; Hydrogen peroxide; Iron(III); OH radical; Picolinic acid; Pyridine

Indexed keywords

EID: 38349131388     PISSN: 10286624     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (45)

1. (a) Barton, D. H. R. (1998), Tetrahedron, 54, 5805; (1997),
2. Pure Appl. Chem. 69, 154; (1996),
3. Chem. Soc. Revs. 237.
4. (b) Barton, D. H. R. and Doller, D. (1992), Acc. Chem. Res. 25, 504.
5. (c) Gozzo, F. (2001), J. Mol. Catal. 171, 1.
6. (d) Schuchardt, U., Carvalho, W. A. and Spinace, E. V. (1993), Synlett. 713.
7. Stavropoulos, P., Celenligil-Cetin, R. and Tapper, A. (2001), Acc. Chem. Res. 34, 745.
8. (b) Kiani, S., Tapper, A. Staples, R. J. and Stavropoulos, P. (2000), J. Am. Chem. Soc. 122, 7503.
9. Newcomb, M., Simakov, P. A. and Park, S. -U. (1996), Tet. Lett. 37, 819.
10. (a) Perkins, M. J. (1996), Chem. Soc. Revs. 229.
11. (b) Knight, C. and. Perkins, M. J. (1991), J. Chem. Soc. Chem. Commun. 925.
12. (a) Minisci, F., Fontana, F., Araneo, S., Recupero, F. and Zhao, L. (1996) Synlett. 119,
13. (b) Minisci, F., Fontana, F., Araneo, S., Recupero, F., Banfi, S. and Quici, S. (1995), J. Am. Chem. Soc. 117, 226
14. (c) Minisci, F., Fontana, F., Araneo, S. and Recupero, F. (1994), Tet. Lett. 35, 3759.
15. (a) MacFaul, P. A., Wayner, D. D. M. and Ingold, K. U. (1998) Acc. Chem. Res. 31, 159.
16. (b) Snelgrove, D. W., MacFaul, P. A., Ingold, K. U. and. Wayner, D. D. M. (1996), Tet. Lett. 37, 823.
17. (c) MacFaul, P. A., Arends, I. W. C. E., Ingold, K. U. and Wayner, D. D. M. (1997), J. Chem. Soc. Perkin Trans 2. 135.
18. (d) MacFaul, P. A., Ingold, K. U. and Wayner, D. D. M. (1997), J. Am. Chem. Soc. 119, 10594.
19. (a) Walling, C. (1998), Acc. Chem. Res. 31, 155.
20. (b) Walling, C. (1975), Acc. Chem. Res. 8, 125.
21. Sawyer, D. T. (1997), Coord. Chem. Revs. 165, 197.
22. Barton, D. H. R., Beviere, S. D., Chavisri, W., Doller, D., Liu, G. and Riebenspies, J. H. (1992), New. J. Chem. 16, 1019.
23. Sobolev, A. P., Babushkin, D. E., Shubin, A. A. and Talsi, E. P.(1996), J. Mol. Catal. A. 112, 253.
24. Jain, S. L. and Bhattacharyya, P. (2005), J. Chem. Soc. Dalton Trans. 2696.
25. th Edition. Longmans, New York
26. Shova, S. G., Brashovyanu, N. V., Turte, K. I. and Mazus, M. D., (1996), Russ J. Coord. Chem. 22, 438.
27. Ingledew, W. J. University of St. Andrews, private communication.
28. GRAFIT is a non-linear least-squares fitting programme supplied by Erithacus Software, Leatherhead, Surrey, UK. The software employs a Marquardt algorithm.
29. The complex set of EPR signals evident in the pyridine solution arises also from the likelihood of mer and facisomers of tris(picolinato)iron(III) in solution along with various bis(picolinato) iron(III) complexes arising from reversible pyridine/water solvolysis reactions.
30. Sawyer, D. T. (1991), Oxygen Chemistry, Oxford University Press, 128.
31. (a) Ingold, K. U. (1969), Acc. Chem. Res. 2, 1.
32. (b) Thomas, J. R. (1966), J. Am. Chem. Soc. 88, 2064.
33. Marr, S. B. and Richens, D. T. (1998), A. C. H. Models in Chemistry 135, 821.
34. (a) Bukowski, M. R., Haffen, H. L., van den Berg, T. A., Halfen, J. A. and Que, L. Jr. (2005), Angew. Chem. Intl. Ed. Eng. 44, 584.
35. (b) Rohde, J. -U. and Que, L. Jr. (2005), Angew. Chem. Intl. Ed. Eng. 44, 2255.
36. (c) Costas, M., Mehn, M. P., Jensen, M. P. and Que, L. Jr. (2004), Chem. Revs. 104, 939.
37. (d) Chen, K., Costas, M., Kim, J., Tipton, A. K. and Que, L. Jr. (2002), J. Am. Chem. Soc. 124, 3026.
38. (e) Chen, K. and Que, L. Jr. (2001), J. Am. Chem. Soc. 123, 6327.
39. (a) Ballard, V., Banse, F., Anxolabehere-Mallart, E., Ghiladi, M., Mattioli, T. A., Philouze, C., Blondin, G. and Girerd, J. -J. (2003), Inorg. Chem. 42, 2470.
40. (b) Hazell, A., McKenzie, C. J., Neilson, L. P., Schindler, S. and Weitzer, M. (2002), J. Chem. Soc. Dalton Trans. 31
41. (a) Yurkova, I. L., Schuchman, H. -P. and von Sonntag, C. (1999), J. Chem. Soc. Perkin Trans 2. 2049,
42. (b) Daniels, J. S. and Gates, K. S. (1996), J. Am. Chem. Soc. 118, 3380.
43. 1 and in a number of other cases OH radicals appear to be involved via Cu(II) see e.g. Lin, T. Y. and Wu, C. H. (2005), J. Catal. 232, 117.
44. Marr, S. B., Carvel, R. O., Richens, D. T., Lee, H. -J., Lane, M. and Stavropoulos, P. (2000), Inorg. Chem. 39, 2685.
45. Jain, S. L., Bhattacharyya, P., Milton, H. L. Slawin, A. M. Z. and Woollins, J. D. (2004), Inorg. Chem. Commun. 7, 423.