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Volumn 125, Issue 34, 2003, Pages 10351-10361

Oxidation of C-H bonds by [(bpy)2(py)RuIVO] 2+ occurs by hydrogen atom abstraction

Author keywords

[No Author keywords available]

Indexed keywords

OXYGEN RADICALS;

EID: 0042932741     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja035276w     Document Type: Article
Times cited : (180)

References (121)
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    • note
    • 2+ per indanone.
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    • note
    • (c) The potentials vs SCE in ref 20a have been converted to NHE by adding 0.24 V.
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    • Representative papers and leading references: (a) Yamada, H.; Hurst, J. K. J. Am. Chem. Soc. 2000, 122, 5303-5311. (b) Farrer, B. T.; Thorp, H. H. Inorg. Chem. 1999, 38, 2497-2502. (c) Muller, J. G.; Acquaye, J. H.; Takeuchi, K. J. Inorg. Chem. 1992, 31, 4552-4557. (d) Gerli, A.; Reedijk, J.; Lakin, M. T.; Spek, A. L.; Inorg. Chem. 1995, 34, 1836-1843. (e) Goldstein, A. S.; Beer, R. H.; Drago, R. S. J. Am. Chem. Soc. 1994, 116, 2424-2429. (f) Dengel, A. C.; El-Hendawy, A. M.; Griffith, W. P.; O'Mahoney, C. A.; Williams, D. J. J. Chem. Soc., Dalton Trans. 1990, 737. (g) Kojima, T. Chem. Lett. 1996, 121-122. (g) Hua, X.; Lappin, A. G. Inorg. Chem. 1995, 34, 992-994. (h) Lau, T. C.; Kochi, J. K. J. Chem. Soc., Chem. Commun. 1987, 798-799. (i) Huynh, M. H. V.; Witham, L. M.; Lasker, J. M.; Wetzler, M.; Mort, B.; Jameson, D. L.; White, P. S.; Takeuchi, K. J.; J. Am. Chem. Soc. 2003, 308-309.
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    • Representative papers and leading references: (a) Yamada, H.; Hurst, J. K. J. Am. Chem. Soc. 2000, 122, 5303-5311. (b) Farrer, B. T.; Thorp, H. H. Inorg. Chem. 1999, 38, 2497-2502. (c) Muller, J. G.; Acquaye, J. H.; Takeuchi, K. J. Inorg. Chem. 1992, 31, 4552-4557. (d) Gerli, A.; Reedijk, J.; Lakin, M. T.; Spek, A. L.; Inorg. Chem. 1995, 34, 1836-1843. (e) Goldstein, A. S.; Beer, R. H.; Drago, R. S. J. Am. Chem. Soc. 1994, 116, 2424-2429. (f) Dengel, A. C.; El-Hendawy, A. M.; Griffith, W. P.; O'Mahoney, C. A.; Williams, D. J. J. Chem. Soc., Dalton Trans. 1990, 737. (g) Kojima, T. Chem. Lett. 1996, 121-122. (g) Hua, X.; Lappin, A. G. Inorg. Chem. 1995, 34, 992-994. (h) Lau, T. C.; Kochi, J. K. J. Chem. Soc., Chem. Commun. 1987, 798-799. (i) Huynh, M. H. V.; Witham, L. M.; Lasker, J. M.; Wetzler, M.; Mort, B.; Jameson, D. L.; White, P. S.; Takeuchi, K. J.; J. Am. Chem. Soc. 2003, 308-309.
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    • Representative papers and leading references: (a) Yamada, H.; Hurst, J. K. J. Am. Chem. Soc. 2000, 122, 5303-5311. (b) Farrer, B. T.; Thorp, H. H. Inorg. Chem. 1999, 38, 2497-2502. (c) Muller, J. G.; Acquaye, J. H.; Takeuchi, K. J. Inorg. Chem. 1992, 31, 4552-4557. (d) Gerli, A.; Reedijk, J.; Lakin, M. T.; Spek, A. L.; Inorg. Chem. 1995, 34, 1836-1843. (e) Goldstein, A. S.; Beer, R. H.; Drago, R. S. J. Am. Chem. Soc. 1994, 116, 2424-2429. (f) Dengel, A. C.; El-Hendawy, A. M.; Griffith, W. P.; O'Mahoney, C. A.; Williams, D. J. J. Chem. Soc., Dalton Trans. 1990, 737. (g) Kojima, T. Chem. Lett. 1996, 121-122. (g) Hua, X.; Lappin, A. G. Inorg. Chem. 1995, 34, 992-994. (h) Lau, T. C.; Kochi, J. K. J. Chem. Soc., Chem. Commun. 1987, 798-799. (i) Huynh, M. H. V.; Witham, L. M.; Lasker, J. M.; Wetzler, M.; Mort, B.; Jameson, D. L.; White, P. S.; Takeuchi, K. J.; J. Am. Chem. Soc. 2003, 308-309.
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    • Representative papers and leading references: (a) Yamada, H.; Hurst, J. K. J. Am. Chem. Soc. 2000, 122, 5303-5311. (b) Farrer, B. T.; Thorp, H. H. Inorg. Chem. 1999, 38, 2497-2502. (c) Muller, J. G.; Acquaye, J. H.; Takeuchi, K. J. Inorg. Chem. 1992, 31, 4552-4557. (d) Gerli, A.; Reedijk, J.; Lakin, M. T.; Spek, A. L.; Inorg. Chem. 1995, 34, 1836-1843. (e) Goldstein, A. S.; Beer, R. H.; Drago, R. S. J. Am. Chem. Soc. 1994, 116, 2424-2429. (f) Dengel, A. C.; El-Hendawy, A. M.; Griffith, W. P.; O'Mahoney, C. A.; Williams, D. J. J. Chem. Soc., Dalton Trans. 1990, 737. (g) Kojima, T. Chem. Lett. 1996, 121-122. (g) Hua, X.; Lappin, A. G. Inorg. Chem. 1995, 34, 992-994. (h) Lau, T. C.; Kochi, J. K. J. Chem. Soc., Chem. Commun. 1987, 798-799. (i) Huynh, M. H. V.; Witham, L. M.; Lasker, J. M.; Wetzler, M.; Mort, B.; Jameson, D. L.; White, P. S.; Takeuchi, K. J.; J. Am. Chem. Soc. 2003, 308-309.
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    • Gerli, A.1    Reedijk, J.2    Lakin, M.T.3    Spek, A.L.4
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    • Representative papers and leading references: (a) Yamada, H.; Hurst, J. K. J. Am. Chem. Soc. 2000, 122, 5303-5311. (b) Farrer, B. T.; Thorp, H. H. Inorg. Chem. 1999, 38, 2497-2502. (c) Muller, J. G.; Acquaye, J. H.; Takeuchi, K. J. Inorg. Chem. 1992, 31, 4552-4557. (d) Gerli, A.; Reedijk, J.; Lakin, M. T.; Spek, A. L.; Inorg. Chem. 1995, 34, 1836-1843. (e) Goldstein, A. S.; Beer, R. H.; Drago, R. S. J. Am. Chem. Soc. 1994, 116, 2424-2429. (f) Dengel, A. C.; El-Hendawy, A. M.; Griffith, W. P.; O'Mahoney, C. A.; Williams, D. J. J. Chem. Soc., Dalton Trans. 1990, 737. (g) Kojima, T. Chem. Lett. 1996, 121-122. (g) Hua, X.; Lappin, A. G. Inorg. Chem. 1995, 34, 992-994. (h) Lau, T. C.; Kochi, J. K. J. Chem. Soc., Chem. Commun. 1987, 798-799. (i) Huynh, M. H. V.; Witham, L. M.; Lasker, J. M.; Wetzler, M.; Mort, B.; Jameson, D. L.; White, P. S.; Takeuchi, K. J.; J. Am. Chem. Soc. 2003, 308-309.
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    • Representative papers and leading references: (a) Yamada, H.; Hurst, J. K. J. Am. Chem. Soc. 2000, 122, 5303-5311. (b) Farrer, B. T.; Thorp, H. H. Inorg. Chem. 1999, 38, 2497-2502. (c) Muller, J. G.; Acquaye, J. H.; Takeuchi, K. J. Inorg. Chem. 1992, 31, 4552-4557. (d) Gerli, A.; Reedijk, J.; Lakin, M. T.; Spek, A. L.; Inorg. Chem. 1995, 34, 1836-1843. (e) Goldstein, A. S.; Beer, R. H.; Drago, R. S. J. Am. Chem. Soc. 1994, 116, 2424-2429. (f) Dengel, A. C.; El-Hendawy, A. M.; Griffith, W. P.; O'Mahoney, C. A.; Williams, D. J. J. Chem. Soc., Dalton Trans. 1990, 737. (g) Kojima, T. Chem. Lett. 1996, 121-122. (g) Hua, X.; Lappin, A. G. Inorg. Chem. 1995, 34, 992-994. (h) Lau, T. C.; Kochi, J. K. J. Chem. Soc., Chem. Commun. 1987, 798-799. (i) Huynh, M. H. V.; Witham, L. M.; Lasker, J. M.; Wetzler, M.; Mort, B.; Jameson, D. L.; White, P. S.; Takeuchi, K. J.; J. Am. Chem. Soc. 2003, 308-309.
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    • Representative papers and leading references: (a) Yamada, H.; Hurst, J. K. J. Am. Chem. Soc. 2000, 122, 5303-5311. (b) Farrer, B. T.; Thorp, H. H. Inorg. Chem. 1999, 38, 2497-2502. (c) Muller, J. G.; Acquaye, J. H.; Takeuchi, K. J. Inorg. Chem. 1992, 31, 4552-4557. (d) Gerli, A.; Reedijk, J.; Lakin, M. T.; Spek, A. L.; Inorg. Chem. 1995, 34, 1836-1843. (e) Goldstein, A. S.; Beer, R. H.; Drago, R. S. J. Am. Chem. Soc. 1994, 116, 2424-2429. (f) Dengel, A. C.; El-Hendawy, A. M.; Griffith, W. P.; O'Mahoney, C. A.; Williams, D. J. J. Chem. Soc., Dalton Trans. 1990, 737. (g) Kojima, T. Chem. Lett. 1996, 121-122. (g) Hua, X.; Lappin, A. G. Inorg. Chem. 1995, 34, 992-994. (h) Lau, T. C.; Kochi, J. K. J. Chem. Soc., Chem. Commun. 1987, 798-799. (i) Huynh, M. H. V.; Witham, L. M.; Lasker, J. M.; Wetzler, M.; Mort, B.; Jameson, D. L.; White, P. S.; Takeuchi, K. J.; J. Am. Chem. Soc. 2003, 308-309.
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    • Representative papers and leading references: (a) Yamada, H.; Hurst, J. K. J. Am. Chem. Soc. 2000, 122, 5303-5311. (b) Farrer, B. T.; Thorp, H. H. Inorg. Chem. 1999, 38, 2497-2502. (c) Muller, J. G.; Acquaye, J. H.; Takeuchi, K. J. Inorg. Chem. 1992, 31, 4552-4557. (d) Gerli, A.; Reedijk, J.; Lakin, M. T.; Spek, A. L.; Inorg. Chem. 1995, 34, 1836-1843. (e) Goldstein, A. S.; Beer, R. H.; Drago, R. S. J. Am. Chem. Soc. 1994, 116, 2424-2429. (f) Dengel, A. C.; El-Hendawy, A. M.; Griffith, W. P.; O'Mahoney, C. A.; Williams, D. J. J. Chem. Soc., Dalton Trans. 1990, 737. (g) Kojima, T. Chem. Lett. 1996, 121-122. (g) Hua, X.; Lappin, A. G. Inorg. Chem. 1995, 34, 992-994. (h) Lau, T. C.; Kochi, J. K. J. Chem. Soc., Chem. Commun. 1987, 798-799. (i) Huynh, M. H. V.; Witham, L. M.; Lasker, J. M.; Wetzler, M.; Mort, B.; Jameson, D. L.; White, P. S.; Takeuchi, K. J.; J. Am. Chem. Soc. 2003, 308-309.
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    • Representative papers and leading references: (a) Yamada, H.; Hurst, J. K. J. Am. Chem. Soc. 2000, 122, 5303-5311. (b) Farrer, B. T.; Thorp, H. H. Inorg. Chem. 1999, 38, 2497-2502. (c) Muller, J. G.; Acquaye, J. H.; Takeuchi, K. J. Inorg. Chem. 1992, 31, 4552-4557. (d) Gerli, A.; Reedijk, J.; Lakin, M. T.; Spek, A. L.; Inorg. Chem. 1995, 34, 1836-1843. (e) Goldstein, A. S.; Beer, R. H.; Drago, R. S. J. Am. Chem. Soc. 1994, 116, 2424-2429. (f) Dengel, A. C.; El-Hendawy, A. M.; Griffith, W. P.; O'Mahoney, C. A.; Williams, D. J. J. Chem. Soc., Dalton Trans. 1990, 737. (g) Kojima, T. Chem. Lett. 1996, 121-122. (g) Hua, X.; Lappin, A. G. Inorg. Chem. 1995, 34, 992-994. (h) Lau, T. C.; Kochi, J. K. J. Chem. Soc., Chem. Commun. 1987, 798-799. (i) Huynh, M. H. V.; Witham, L. M.; Lasker, J. M.; Wetzler, M.; Mort, B.; Jameson, D. L.; White, P. S.; Takeuchi, K. J.; J. Am. Chem. Soc. 2003, 308-309.
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    • Representative papers and leading references: (a) Yamada, H.; Hurst, J. K. J. Am. Chem. Soc. 2000, 122, 5303-5311. (b) Farrer, B. T.; Thorp, H. H. Inorg. Chem. 1999, 38, 2497-2502. (c) Muller, J. G.; Acquaye, J. H.; Takeuchi, K. J. Inorg. Chem. 1992, 31, 4552-4557. (d) Gerli, A.; Reedijk, J.; Lakin, M. T.; Spek, A. L.; Inorg. Chem. 1995, 34, 1836-1843. (e) Goldstein, A. S.; Beer, R. H.; Drago, R. S. J. Am. Chem. Soc. 1994, 116, 2424-2429. (f) Dengel, A. C.; El-Hendawy, A. M.; Griffith, W. P.; O'Mahoney, C. A.; Williams, D. J. J. Chem. Soc., Dalton Trans. 1990, 737. (g) Kojima, T. Chem. Lett. 1996, 121-122. (g) Hua, X.; Lappin, A. G. Inorg. Chem. 1995, 34, 992-994. (h) Lau, T. C.; Kochi, J. K. J. Chem. Soc., Chem. Commun. 1987, 798-799. (i) Huynh, M. H. V.; Witham, L. M.; Lasker, J. M.; Wetzler, M.; Mort, B.; Jameson, D. L.; White, P. S.; Takeuchi, K. J.; J. Am. Chem. Soc. 2003, 308-309.
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    • Huynh, M.H.V.1    Witham, L.M.2    Lasker, J.M.3    Wetzler, M.4    Mort, B.5    Jameson, D.L.6    White, P.S.7    Takeuchi, K.J.8
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    • Mayer, J. M. In ref 1c, pp 1-43.
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    • note
    • a are measured in water and C = -57 ± 2.
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    • note
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    • See, for instance: (a) References 1c, 23-26, 29, 38a
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    • Number 69-July
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    • (2001) NIST Standard Reference Database
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    • Reference 39h and references therein
    • (a) Reference 39h and references therein.
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    • 2 gives optically active 1-chloro-1-phenylpropane in 35-40% chemical yield and with about 35% retention of configuration: Stephenson, L. M.; Egnatchik, J.; Speth, D. R. J. Org. Chem. 1979, 44, 346-349. (c) Permanganate oxidations of arylvaleric acids gave 30-40% retention: Brauman, J. I.; Pandell, A. J. J. Am. Chem. Soc. 1970, 92, 329-335. See also: (d) Wiberg, K. B.; Fox, A. S. J. Am. Chem, Soc. 1963, 85, 3487. (e) Eastman, R. H.; Quinn, R. A. J. Am. Chem. Soc. 1960, 82, 4249.
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    • 2 gives optically active 1-chloro-1-phenylpropane in 35-40% chemical yield and with about 35% retention of configuration: Stephenson, L. M.; Egnatchik, J.; Speth, D. R. J. Org. Chem. 1979, 44, 346-349. (c) Permanganate oxidations of arylvaleric acids gave 30-40% retention: Brauman, J. I.; Pandell, A. J. J. Am. Chem. Soc. 1970, 92, 329-335. See also: (d) Wiberg, K. B.; Fox, A. S. J. Am. Chem, Soc. 1963, 85, 3487. (e) Eastman, R. H.; Quinn, R. A. J. Am. Chem. Soc. 1960, 82, 4249.
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    • 2 gives optically active 1-chloro-1-phenylpropane in 35-40% chemical yield and with about 35% retention of configuration: Stephenson, L. M.; Egnatchik, J.; Speth, D. R. J. Org. Chem. 1979, 44, 346-349. (c) Permanganate oxidations of arylvaleric acids gave 30-40% retention: Brauman, J. I.; Pandell, A. J. J. Am. Chem. Soc. 1970, 92, 329-335. See also: (d) Wiberg, K. B.; Fox, A. S. J. Am. Chem, Soc. 1963, 85, 3487. (e) Eastman, R. H.; Quinn, R. A. J. Am. Chem. Soc. 1960, 82, 4249.
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    • 2 gives optically active 1-chloro-1-phenylpropane in 35-40% chemical yield and with about 35% retention of configuration: Stephenson, L. M.; Egnatchik, J.; Speth, D. R. J. Org. Chem. 1979, 44, 346-349. (c) Permanganate oxidations of arylvaleric acids gave 30-40% retention: Brauman, J. I.; Pandell, A. J. J. Am. Chem. Soc. 1970, 92, 329-335. See also: (d) Wiberg, K. B.; Fox, A. S. J. Am. Chem, Soc. 1963, 85, 3487. (e) Eastman, R. H.; Quinn, R. A. J. Am. Chem. Soc. 1960, 82, 4249.
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    • 2 gives optically active 1-chloro-1-phenylpropane in 35-40% chemical yield and with about 35% retention of configuration: Stephenson, L. M.; Egnatchik, J.; Speth, D. R. J. Org. Chem. 1979, 44, 346-349. (c) Permanganate oxidations of arylvaleric acids gave 30-40% retention: Brauman, J. I.; Pandell, A. J. J. Am. Chem. Soc. 1970, 92, 329-335. See also: (d) Wiberg, K. B.; Fox, A. S. J. Am. Chem, Soc. 1963, 85, 3487. (e) Eastman, R. H.; Quinn, R. A. J. Am. Chem. Soc. 1960, 82, 4249.
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    • Eastman, R.H.1    Quinn, R.A.2
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    • (a) This argument is related to one made by Groves, personal communication, ref 39h, and Brazeau, B. J.; Austin, R. N.; Tarr, C.; Groves, J. T.; Lipscomb, J. D. J. Am. Chem. Soc. 2001, 123, 11 831-11 837. (b) Related arguments have been in the context of dioxirane oxidations, cf., Curci, R.; Dinoi, A.; Fusco, C.; Lillo, M. A. Tetr. Lett. 1996, 37, 249-252.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 11831-11837
    • Brazeau, B.J.1    Austin, R.N.2    Tarr, C.3    Groves, J.T.4    Lipscomb, J.D.5
  • 115
    • 0030044090 scopus 로고    scopus 로고
    • (a) This argument is related to one made by Groves, personal communication, ref 39h, and Brazeau, B. J.; Austin, R. N.; Tarr, C.; Groves, J. T.; Lipscomb, J. D. J. Am. Chem. Soc. 2001, 123, 11 831-11 837. (b) Related arguments have been in the context of dioxirane oxidations, cf., Curci, R.; Dinoi, A.; Fusco, C.; Lillo, M. A. Tetr. Lett. 1996, 37, 249-252.
    • (1996) Tetr. Lett. , vol.37 , pp. 249-252
    • Curci, R.1    Dinoi, A.2    Fusco, C.3    Lillo, M.A.4
  • 118
    • 0042374347 scopus 로고    scopus 로고
    • note
    • xy = 0.98.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.