Kinetic isotope effects for electron-transfer pathways in the oxidative C-H activation of hydrocarbons

Journal of the American Chemical Society

Volumn 120, Issue 12, 1998, Pages 2826-2830

  Bockman, T M ^a   Hubig, S M ^a   Kochi, J K ^a  

^a University of Houston   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROCARBON; HYDROGEN; TOLUENE; UBIDECARENONE;

ARTICLE; CHEMICAL BINDING; CROSS LINKING; ELECTRON TRANSPORT; OXIDATION;

EID: 0032054091     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja974205s     Document Type: Article

References (55)

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48. The mechanistic ambiguity addressed in this study applies to other hydrogen-atom transfer reactions, as well as a wide variety of organic processes for which an initial electron-transfer process may be formulated. For H-atom transfers, see: (a) Patz, M.: Fukuzumi, S. J. Phys. Org. Chem. 1997, 10, 129. For other reactions, see: (b) Olah, G. A.; Malhotra, R.; Narang, S. C. Nitration: Methods and Mechanism; VCH: New York, 1989; p 166 f (nitration). (c) Baciocchi, E.; Galli, C. J. Phys. Org. Chem. 1995, 8, 563 (halogenation). (d) Tolbert, L. M.; Sun, X. J.; Ashby, E. C. J. Am. Chem. Soc. 1995, 117, 2681 (nucleophilic substitution). (e) Freilich, S. C.; Peters, K. S. J. Am. Chem. Soc. 1985, 107, 3819 (cycloaddition). (f) Lopez, L.; Troisi, L. Tetrahedron Lett. 1989, 30, 3097 (rearrangement of epoxides). For organometallic examples, see: (g) Astruc, D. Electron Transfer and Radical Processes in Transition-Metal Chemistry; VCH: New York, 1995.
49. The mechanistic ambiguity addressed in this study applies to other hydrogen-atom transfer reactions, as well as a wide variety of organic processes for which an initial electron-transfer process may be formulated. For H-atom transfers, see: (a) Patz, M.: Fukuzumi, S. J. Phys. Org. Chem. 1997, 10, 129. For other reactions, see: (b) Olah, G. A.; Malhotra, R.; Narang, S. C. Nitration: Methods and Mechanism; VCH: New York, 1989; p 166 f (nitration). (c) Baciocchi, E.; Galli, C. J. Phys. Org. Chem. 1995, 8, 563 (halogenation). (d) Tolbert, L. M.; Sun, X. J.; Ashby, E. C. J. Am. Chem. Soc. 1995, 117, 2681 (nucleophilic substitution). (e) Freilich, S. C.; Peters, K. S. J. Am. Chem. Soc. 1985, 107, 3819 (cycloaddition). (f) Lopez, L.; Troisi, L. Tetrahedron Lett. 1989, 30, 3097 (rearrangement of epoxides). For organometallic examples, see: (g) Astruc, D. Electron Transfer and Radical Processes in Transition-Metal Chemistry; VCH: New York, 1995.
50. The mechanistic ambiguity addressed in this study applies to other hydrogen-atom transfer reactions, as well as a wide variety of organic processes for which an initial electron-transfer process may be formulated. For H-atom transfers, see: (a) Patz, M.: Fukuzumi, S. J. Phys. Org. Chem. 1997, 10, 129. For other reactions, see: (b) Olah, G. A.; Malhotra, R.; Narang, S. C. Nitration: Methods and Mechanism; VCH: New York, 1989; p 166 f (nitration). (c) Baciocchi, E.; Galli, C. J. Phys. Org. Chem. 1995, 8, 563 (halogenation). (d) Tolbert, L. M.; Sun, X. J.; Ashby, E. C. J. Am. Chem. Soc. 1995, 117, 2681 (nucleophilic substitution). (e) Freilich, S. C.; Peters, K. S. J. Am. Chem. Soc. 1985, 107, 3819 (cycloaddition). (f) Lopez, L.; Troisi, L. Tetrahedron Lett. 1989, 30, 3097 (rearrangement of epoxides). For organometallic examples, see: (g) Astruc, D. Electron Transfer and Radical Processes in Transition-Metal Chemistry; VCH: New York, 1995.
51. The mechanistic ambiguity addressed in this study applies to other hydrogen-atom transfer reactions, as well as a wide variety of organic processes for which an initial electron-transfer process may be formulated. For H-atom transfers, see: (a) Patz, M.: Fukuzumi, S. J. Phys. Org. Chem. 1997, 10, 129. For other reactions, see: (b) Olah, G. A.; Malhotra, R.; Narang, S. C. Nitration: Methods and Mechanism; VCH: New York, 1989; p 166 f (nitration). (c) Baciocchi, E.; Galli, C. J. Phys. Org. Chem. 1995, 8, 563 (halogenation). (d) Tolbert, L. M.; Sun, X. J.; Ashby, E. C. J. Am. Chem. Soc. 1995, 117, 2681 (nucleophilic substitution). (e) Freilich, S. C.; Peters, K. S. J. Am. Chem. Soc. 1985, 107, 3819 (cycloaddition). (f) Lopez, L.; Troisi, L. Tetrahedron Lett. 1989, 30, 3097 (rearrangement of epoxides). For organometallic examples, see: (g) Astruc, D. Electron Transfer and Radical Processes in Transition-Metal Chemistry; VCH: New York, 1995.
52. The mechanistic ambiguity addressed in this study applies to other hydrogen-atom transfer reactions, as well as a wide variety of organic processes for which an initial electron-transfer process may be formulated. For H-atom transfers, see: (a) Patz, M.: Fukuzumi, S. J. Phys. Org. Chem. 1997, 10, 129. For other reactions, see: (b) Olah, G. A.; Malhotra, R.; Narang, S. C. Nitration: Methods and Mechanism; VCH: New York, 1989; p 166 f (nitration). (c) Baciocchi, E.; Galli, C. J. Phys. Org. Chem. 1995, 8, 563 (halogenation). (d) Tolbert, L. M.; Sun, X. J.; Ashby, E. C. J. Am. Chem. Soc. 1995, 117, 2681 (nucleophilic substitution). (e) Freilich, S. C.; Peters, K. S. J. Am. Chem. Soc. 1985, 107, 3819 (cycloaddition). (f) Lopez, L.; Troisi, L. Tetrahedron Lett. 1989, 30, 3097 (rearrangement of epoxides). For organometallic examples, see: (g) Astruc, D. Electron Transfer and Radical Processes in Transition-Metal Chemistry; VCH: New York, 1995.
53. The mechanistic ambiguity addressed in this study applies to other hydrogen-atom transfer reactions, as well as a wide variety of organic processes for which an initial electron-transfer process may be formulated. For H-atom transfers, see: (a) Patz, M.: Fukuzumi, S. J. Phys. Org. Chem. 1997, 10, 129. For other reactions, see: (b) Olah, G. A.; Malhotra, R.; Narang, S. C. Nitration: Methods and Mechanism; VCH: New York, 1989; p 166 f (nitration). (c) Baciocchi, E.; Galli, C. J. Phys. Org. Chem. 1995, 8, 563 (halogenation). (d) Tolbert, L. M.; Sun, X. J.; Ashby, E. C. J. Am. Chem. Soc. 1995, 117, 2681 (nucleophilic substitution). (e) Freilich, S. C.; Peters, K. S. J. Am. Chem. Soc. 1985, 107, 3819 (cycloaddition). (f) Lopez, L.; Troisi, L. Tetrahedron Lett. 1989, 30, 3097 (rearrangement of epoxides). For organometallic examples, see: (g) Astruc, D. Electron Transfer and Radical Processes in Transition-Metal Chemistry; VCH: New York, 1995.
54. The mechanistic ambiguity addressed in this study applies to other hydrogen-atom transfer reactions, as well as a wide variety of organic processes for which an initial electron-transfer process may be formulated. For H-atom transfers, see: (a) Patz, M.: Fukuzumi, S. J. Phys. Org. Chem. 1997, 10, 129. For other reactions, see: (b) Olah, G. A.; Malhotra, R.; Narang, S. C. Nitration: Methods and Mechanism; VCH: New York, 1989; p 166 f (nitration). (c) Baciocchi, E.; Galli, C. J. Phys. Org. Chem. 1995, 8, 563 (halogenation). (d) Tolbert, L. M.; Sun, X. J.; Ashby, E. C. J. Am. Chem. Soc. 1995, 117, 2681 (nucleophilic substitution). (e) Freilich, S. C.; Peters, K. S. J. Am. Chem. Soc. 1985, 107, 3819 (cycloaddition). (f) Lopez, L.; Troisi, L. Tetrahedron Lett. 1989, 30, 3097 (rearrangement of epoxides). For organometallic examples, see: (g) Astruc, D. Electron Transfer and Radical Processes in Transition-Metal Chemistry; VCH: New York, 1995.
55. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon: Oxford, 1988.