Reactivity studies of biomimetic catalytic epoxidation of alkenes with tetrabutylammonium periodate in the presence of various manganese porphyrins and nitrogen donors: Significant axial ligand π-bonding effects

New Journal of Chemistry

Volumn 28, Issue 6, 2004, Pages 740-747

  Mohajer, Daryoush ^a   Karimipour, Gholamreza ^a   Bagherzadeh, Mojtaba ^b  

^a SHIRAZ UNIVERSITY   (Iran)

^b SHARIF UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

1 METHYLIMIDAZOLE; ALKENE; AMINE; AMINOPYRIDINE DERIVATIVE; BIOMIMETIC MATERIAL; FLUORINE DERIVATIVE; IMIDAZOLE; IMIDAZOLE DERIVATIVE; LIGAND; MANGANESE DERIVATIVE; NITROGEN; PERIODATE; PHENYL GROUP; PICOLINE DERIVATIVE; PYRIDINE DERIVATIVE; TETRABUTYLAMMONIUM; TETRAPHENYLPORPHYRIN DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL INTERACTION; CORRELATION ANALYSIS; ELECTRON; EPOXIDATION; HYDROGEN BOND; PRIORITY JOURNAL;

EID: 3042700248     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/b310909g     Document Type: Article

References (73)

1. (a) D. Mansuy and P. Battioni, in The Porphyrin Handbook, eds. K. M. Kadish, K. M. Smith and R. Guilard, Academic Press, San Diego, 2000, vol. 4, ch. 26, p. 1;
2. (b) J. T. Groves, K. Shalyaev and J. Lee, in The Porphyrin Handbook, eds. K. M. Kadish, K. M. Smith and R. Guilard, Academic Press, San Diego, 1999, ch. 27, p. 17;
3. (c) D. Dolphin, T. G. Traylor and L. Y. Xie, Acc. Chem. Res., 1997, 30, 251;
4. (d) P. Bhyrappa, J. K. Young, J. S. Moore and K. S. Suslick, J. Mol. Catal. A: Chem., 1996, 113, 109;
5. (e) A. Maldotti, A. Molinari, P. Bergamini, R. Amadelli and D. Mansuy, J. Mol. Catal. A: Chem., 1996, 113, 147;
6. (f) D. Mansuy, Coord. Chem. Rev., 1993, 125, 129;
7. (g) B. Meunier, Chem. Rev., 1992, 92, 1411;
8. (h) I. Tabushi, Coord. Chem. Rev., 1988, 86, 1;
9. (i) T. J. McMurry and J. T. Groves, Cytochrome P-450: Mechanism and Biochemistry, ed. P. R. Ortiz de Montellano, Plenum Press, New York and London, 1986, ch. 1.
10. (a) D. Mohajer, R. Tayebee and H. Goudarziafshar, J. Chem. Res., 1999, (S) 168;
11. (b) R. D. Arasasingham, G. X. He and T. C. Bruice, J. Am. Chem. Soc., 1993, 115, 7985;
12. (c) P. Battioni, J. P. Renaud, J. F. Bartoli, M. Reins-Artiles, M. Fort and D. Mansuy, J. Am. Chem. Soc., 1988, 110, 8462;
13. (d) J. P. Collman, J. I. Brauman, B. Meunier, T. Hayashi, T. Kodadek and S. A. Raybuck, J. Am. Chem. Soc., 1985, 107, 2000;
14. (e) B. de Poorter and B. Meunier, J. Chem. Soc., Perkin Trans. 2, 1985, 1735;
15. (f) J. R. Lindsay-Smith and P. R. Sleath, J. Chem. Soc., Perkin Trans. 2, 1982, 1009;
16. (g) J. T. Groves, T. E. Nemo and R. S. Myers, J. Am. Chem. Soc., 1979, 101, 1032.
17. (a) D. Mohajer and A. Rezaeifard, Tetrahedron Lett., 2002, 43, 1881;
18. (b) J. P. Collman, J. I. Brauman, J. P. Fitzgerald, P. D. Hampton, Y. Naruta and T. Michida, Bull. Chem. Soc. Jpn., 1998, 61, 47;
19. (c) Z. Gross and S. Ini, J. Org. Chem., 1997, 62, 5514;
20. (d) D. Mohajer and S. Tangestaninejad, Tetrahedron Lett., 1994, 35, 945;
21. (e) Y. Naruta and K. Maruyama, Tetrahedron Lett., 1987, 28, 4553.
22. (a) D. Ostavic and T. C. Bruice, Acc. Chem. Res., 1992, 25, 314;
23. (b) D. Ostavic and T. C. Bruice, J. Am. Chem. Soc., 1989, 111, 6511;
24. (c) J. T. Groves and T. E. Nemo, J. Am. Chem. Soc., 1983, 105, 5786.
25. (a) J. Y. Liu, X. F. Li, Y. Z. Li, W. B. Chang and A. J. Huang, J. Mol. Catal. A: Chem., 2002, 187, 163;
26. (b) E. Baciocchi, T. Boschi, C. Galli, A. Lapi and P. Tagliatesta, Tetrahedron, 1997, 53, 4497;
27. (c) K. Konishi, K. Oda, K. Nishida, T. Aida and S. Inoue, J. Am. Chem. Soc., 1992, 114, 1313;
28. (d) R. L. Halterman and S. T. Jan, J. Org. Chem., 1991, 56, 5253;
29. (e) J. P. Battioni, D. Dupre and D. Mansuy, J. Organomet. Chem., 1987, 328, 173;
30. (f) D. Mansuy, Pure Appl. Chem., 1987, 59, 759;
31. (g) E. Guilmet and B. Meunier, Tetrahedron Lett., 1982, 23, 2449;
32. (h) E. Guilmet and B. Meunier, Nouv. J. Chim., 1982, 6, 511.
33. J. P. Collman, A. S. Chien, T. A. Eberspacher, M. Zhong and J. I. Brauman, Inorg. Chem., 2000, 39, 4625.
34. (a) B. M. Trost and R. Braslau, J. Org. Chem., 1988, 53, 532;
35. (b) A. Robert and B. Meunier, New. J. Chem., 1988, 12, 885;
36. (c) R. J. Kennedy and A. M. Stock, J. Org. Chem., 1960, 25, 1901.
37. S. Banfi, F. Montanari and S. Quici, J. Org. Chem., 1989, 54, 1850.
38. E. M. Davoras and A. G. Coutsolelos, J. Inorg. Biochem., 2003, 94, 161.
39. (a) M. K. Safo, F. A. Walker, A. M. Raitsimring, W. P. Walters, D. P. Dolata, P. G. Debrunner and W. R. Scheidt, J. Am. Chem. Soc., 1994, 116, 7760;
40. (b) M. K. Safo, G. P. Gupta, C. T. Watson, U. Simonis, F. A. Walker and W. R. Scheidt, J. Am. Chem. Soc., 1992, 114, 7066;
41. (c) M. K. Safo, G. P. Gupta, F. A. Walker and W. R. Scheidt, J. Am. Chem. Soc., 1991, 113, 5497.
42. H. C. Brown and X. R. Mihm, J. Am. Chem. Soc., 1955, 77, 1723.
43. B. Meunier, E. Guilmet, M.-E. De Carvalho and R. Poilblanc, J. Am. Chem. Soc., 1984, 106, 6668.
44. (a) G. C. Cole and A. C. Legon, Chem. Phys. Lett., 2003, 369, 31;
45. (b) F. Grepioni, G. Cojazzi, S. M. Draper, N. Scully and D. Braga, Organometallics, 1998, 17, 296.
46. C. K. Chang and T. G. Traylor, J. Am. Chem. Soc., 1973, 95, 8477.
47. (a) L. C. Yuan and T. C. Bruice, J. Am. Chem. Soc., 1986, 108, 1643;
48. (b) P. Obrien and D. A. Sweigart, Inorg. Chem., 1985, 24, 1405;
49. (c) F. A. Walker, M. W. Lo and M. T. Ree, J. Am. Chem. Soc., 1976, 98, 5552.
50. (a) G. B. Jameson and J. A. Ibers, in Bioinorganic Chemistry, eds. I. Bertini, H. B. Gray, S. Lippard and J. Valentine, University Science Books, 20 Edgehill Road, Mill Valley, CA 94941, 1994, ch. 4, p. 167;
51. (b) G. A. Tondreau and D. A. Sweigart, Inorg. Chem., 1984, 23, 1060.
52. D. V. Stynes, H. C. Stynes, B. R. James and J. A. Ibers, J. Am. Chem. Soc., 1973, 95, 1796.
53. D. Mohajer and M. Bagherzadeh, J. Chem. Res., 1998, (S) 556.
54. M. F. Powell, E. F. Pai and T. C. Bruice, J. Am. Chem. Soc., 1984, 106, 3277.
55. (a) J. T. Groves, W. J. Kruper, Jr. and R. C. Haushalter, J. Am. Chem. Soc., 1980, 102, 6375;
56. (b) Y. Iamamoto, M. D. Assis, K. J. Ciuffi, C. M. C. Prado, B. Z. Prellwitz, M. Moraes, O. R. Nascimento and H. C. Sacco, J. Mol. Catal. A: Chem., 1997, 116, 365.
57. G. N. La Mar and F. A. Walker, J. Am. Chem. Soc., 1975, 97, 5103.
58. W. R. Scheidt and D. M. Chipman, J. Am. Chem. Soc., 1986, 108, 1163.
59. (a) Y. Iamamoto, M. D. Assis, K. J. Ciuffi, H. C. Sacco, L. Iwamoto, A. J. B. Melo, O. R. Nascimento and C. M. Prado, J. Mol. Catal. A: Chem., 1996, 109, 189;
60. (b) M. J. Nappa and C. A. Tolman, Inorg. Chem., 1985, 24, 4711.
61. D. M. Collins, R. Countryman and J. L. Hoard, J. Am. Chem. Soc., 1972, 94, 2066.
62. W. Nam, S. W. Jin, M. H. Lim, J. Y. Ryu and C. Kim, Inorg. Chem., 2002, 41, 3647.
63. A. D. Adler, F. R. Longo, J. D. Finarelli, J. Goldmacher, J. Assour and L. Korsakoff, J. Org. Chem., 1967, 32, 476.
64. A. Bettelheim, B. A. White, S. A. Raybuck and R. W. Murray, Inorg. Chem., 1987, 26, 1009.
65. P. Hoffmann, A. Robert and B. Meunier, Bull. Soc. Chim. Fr., 1992, 129, 85.
66. J. S. Lindsey, I. C. Schreiman, H. C. Hsu, P. C. Kearney and A. M. Marguerettaz, J. Org. Chem., 1987, 52, 827.
67. A. D. Adler, F. R. Longo, F. Kampas and J. Kim, J. Inorg. Nucl. Chem., 1970, 32, 2443.
68. K. M. Kadish, C. Araullo-McAdams, B. C. Han and M. M. Franzen, J. Am. Chem. Soc., 1990, 112, 8364.
69. D. D. Perrin, W. L. F. Armarego, D. R. Perrin, Purification of Laboratory Chemicals, Pergamon Press, Elmsford, NY, 2nd edn., 1980.
70. R. L. David, Handbook of Chemistry and Physics, CRC Press, New York, 80th edn., 1999-2000, pp. 8, 46-56.
71. K. Schofield, Hetero-Aromatic Nitrogen Compounds, Pyrroles and Pyridines, Plenum Press, New York, 1967, p. 146.
72. A. Albert, in Physical Methods in Heterocyclic Chemistry, ed. A. R. Katritzky, Academic Press, New York, 1971, Vol III, p. 1-26.
73. K. Hoffmann, Imidazole and its Derivatives, Interscience Publishers Inc., New York, 1953, Part I, p. 15.