Regioselectivity in 2-methylbutane hydroxylation mediated by FeO+ and FeO2+

Organometallics

Volumn 20, Issue 7, 2001, Pages 1397-1407

  Yumura, Takashi ^a   Yoshizawa, Kazunari ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROCARBON HYDROXYLATION; KINETIC ISOTOPE EFFECTS; METHYLBUTANE HYDROXYLATION; REGIOSELECTIVITY; TRANSITION STATE THEORY;

BUTANE; CATALYST SELECTIVITY; CHEMICAL BONDS; DISSOCIATION; HYDROXYLATION; PHASE TRANSITIONS; PROBABILITY DENSITY FUNCTION; STEREOCHEMISTRY; THERMODYNAMICS;

IRON COMPOUNDS;

EID: 0035795443     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om000811b     Document Type: Article

References (62)

1. (a) Shilov, A. E. The Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reidel: Dordrecht, The Netherlands 1984.
2. (b) Shilov, A. E. Metal Complexes in Biomimetic Chemical Reactions; CRC: Boca Raton, FL, 1996.
3. (a) Bergman, R. G. Science 1984, 223, 902.
4. (b) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154.
5. Hill, C. L., Ed. Activation and Functionalization of Alkanes; Wiley: New York, 1989.
6. Davies, J. A.; Watson, P. L.; Liebman, J. F.; Greenberg, A. Selective Hydrocarbon Activation; VCH: New York, 1990.
7. (a) Crabtree, R. H. Chem. Rev. 1985, 85, 245.
8. (b) Crabtree, R. H. Chem. Rev. 1995, 95, 987.
9. Gesser, H. D.; Hunter, N. R.; Prakash, C. B. Chem. Rev. 1985, 85, 237.
10. Lunsford, J. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 970.
11. Schneider, J. J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1068.
12. Hall, C.; Perutz, R. N. Chem. Rev. 1996, 96, 3125.
13. (a) Cytochrome P450: Structure, Mechanism, and Biochemistry, 2nd ed.; Ortiz de Montellano, P. R., Ed.; Plenum: New York, 1995.
14. (b) Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841.
15. (a) Wallar, B. J.; Lipscomb, J. D. Chem. Rev. 1996, 96, 2625.
16. (b) Que, L., Jr.; Dong, Y. Acc. Chem. Res. 1996, 29, 190.
17. (c) Feig, A. L.; Lippard, S. J. Chem. Rev. 1994, 94, 759.
18. (d) Lipscomb, J. D. Annu. Rev. Microbiol. 1994, 48, 371.
19. Schröder, D.; Schwarz, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1973.
20. (a) Schröder, D.; Schwarz, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1433.
21. (b) Schröder, D.; Fiedler, A.; Hrusák, J.; Schwarz, H. J. Am. Chem. Soc. 1992, 114, 1215.
22. (c) Schröder, D.; Schwarz, H.; Clemmer, D. E.; Chen, Y.-M.; Armentrout, P. B.; Baranov, V. I.; Böhme, D. K. Int. J. Mass Spectrom. Ion Processes 1997, 161, 175.
23. (a) Schröder, D.; Schwarz, H. Helv. Chim. Acta 1992, 75, 1281.
24. (b) Becker, H.; Schröder, D.; Zummack, W.; Schwarz, H. J. Am. Chem. Soc. 1994, 116, 1096.
25. (c) Ryan, M. F.; Stöckigt, D.; Schwarz, H. J. Am. Chem. Soc. 1994, 116, 9565.
26. (a) Kappes, M. M.; Staley, R. H. J. Am. Chem. Soc. 1981, 103, 1286.
27. (b) Kappes, M. M.; Staley, R. H. J. Phys. Chem. 1981, 85, 942.
28. (a) Yoshizawa, K.; Shiota, Y.; Yamabe, T. Chem. Eur. J. 1997, 3, 1160.
29. (b) Yoshizawa, K.; Shiota, Y.; Yamabe, T. J. Am. Chem. Soc. 1998, 120, 564.
30. (c) Yoshizawa, K.; Shiota, Y.; Yamabe, T. Organometallics 1998, 17, 2825.
31. Choi, S.-Y.; Eaton, P. E.; Hollenberg, P. F.; Liu, K. E.; Lippard, S. J.; Newcomb, M. Putt, D. A.; Upadhyaya, S. P.; Xiong, Y. J. Am. Chem. Soc. 1996, 118, 6547.
32. Jin, Y.; Lipscomb, J. D. Biochemistry 1999, 38, 6178.
33. Choi, S.-Y.; Eaton, P. E.; Kopp, D. A.; Lippard, S. J.; Newcomb, M.; Shen, R. J. Am. Chem. Soc. 1999, 121, 12198.
34. (a) McMillen, D. F.; Golden, D. M. Annu. Rev. Phys. Chem. 1982, 33, 493.
35. (b) Solomons, T. W. G. Organic Chemistry, 5th ed.; Wiley: New York, 1996.
36. Faber, K. Biotransformations in Organic Chemistry, 3rd ed.; Springer-Verlag: Berlin, 1997.
37. (a) Schwarz, J.; Schwarz, H. Helv. Chim. Acta 1995, 78, 1013.
38. (b) Harris, N.; Shaik, S.; Schröder, D.; Schwarz, H. Helv. Chim. Acta 1999, 82, 1784.
39. (a) Shaik, S.; Danovich, D.; Fiedler, A.; Schröder, D.; Schwarz, H. Helv. Chim. Acta 1995, 78, 1393.
40. (b) Schröder, D.; Shaik, S.; Schwarz, H. Acc. Chem. Res. 2000, 33, 139.
41. (a) Holthausen, M. C.; Fiedler, A.; Schwarz, H.; Koch, W. J. Phys. Chem. 1996, 100, 6236.
42. (b) Holthausen, M. C.; Koch, W. J. Am. Chem. Soc. 1996, 118, 9932.
43. (c) Holthausen, M. C.; Koch, W. Helv. Chim. Acta 1996, 79, 1939.
44. (a) Carroll, J. J.; Haug, K. L.; Weisshaar, J. C.; Blomberg, M.R.A.; Siegbahn, P.E.M.; Svensson, M. J. Phys. Chem. 1995, 99, 13955.
45. Carroll, J. J.; Weisshaar, J. C.; Siegbahn, P. E. M.; Wittborn, C. A. M.; Blomberg, M. R. A. J. Phys. Chem. 1995, 99, 14388.
46. (c) Yi, S. S.; Blomberg, M. R. A.; Siegbahn, P. E. M.; Weisshaar, J. C. J. Phys. Chem. A 1998, 102, 395.
47. (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098.
48. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
49. (c) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623.
50. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
51. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94; Gaussian Inc.: Pittsburgh, PA, 1995.
52. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200.
53. Wachters, A. J. H. J. Chem. Phys. 1970, 52, 1033.
54. Dunning, T. H.; Hay, P. J. In Modern Theoretical Chemistry; Schaefer, H. F., Ed.; Plenum: New York, 1976.
55. Loh, S. K.; Fisher, E. R.; Lian, L.; Schultz, R. H.; Armentrout, P. B. J. Phys. Chem. 1989, 93, 2601.
56. (a) McQuarrie, D. A. Statistical Thermodynamics; University Science Books: Mill Valley, CA 1973.
57. (b) Filatov, M.; Shaik, S. J. Phys. Chem. A 1998, 102, 3835.
58. Castelhano, A. L.; Griller, D. J. Am. Chem. Soc. 1982, 104, 3655.
59. 4Δ state from CASPT2D calculations. However, this discrepancy is not so important is discussing the energy profile of the quartet reaction pathway because the relevant reaction species have no symmetry.
60. 4Δ) in paths 2 and 3, respectively.
61. Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc. 1994, 116, 6459.
62. ‡ is the imaginary frequency relevant to a transition state.