Hydrogen Atom Abstraction by Permanganate: Oxidations of Arylalkanes in Organic Solvents

Inorganic Chemistry

Volumn 36, Issue 10, 1997, Pages 2069-2078

  Gardner, Kimberly A ^a   Kuehnert, Linda L ^a   Mayer, James M ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000166551     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic961297y     Document Type: Article

References (129)

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56. 32
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86. See, for instance, refs 1 and 3 and the following: (a) Stubbe, J.; Kozarich, J. W. Chem. Rev. 1987, 87, 1107-1136. (b) Hecht, S. M. Acc. Chem. Res. 1986, 19, 383-391. Stewart, L. C.; Klinman, J. P. Annu. Rev. Biochem. 1988, 57, 551-592. Tian, G.; Berry, J. A.; Klinman, J. P. Biochemistry 1994, 33, 226-234. (e) Lin, C. H.; Ito, T.; Wang, J.-X.; Lunsford, J. H. J. Am. Chem. Soc. 1987, 109, 4808 and references therein.
87. See, for instance, refs 1 and 3 and the following: (a) Stubbe, J.; Kozarich, J. W. Chem. Rev. 1987, 87, 1107-1136. (b) Hecht, S. M. Acc. Chem. Res. 1986, 19, 383-391. Stewart, L. C.; Klinman, J. P. Annu. Rev. Biochem. 1988, 57, 551-592. Tian, G.; Berry, J. A.; Klinman, J. P. Biochemistry 1994, 33, 226-234. (e) Lin, C. H.; Ito, T.; Wang, J.-X.; Lunsford, J. H. J. Am. Chem. Soc. 1987, 109, 4808 and references therein.
88. See, for instance, refs 1 and 3 and the following: (a) Stubbe, J.; Kozarich, J. W. Chem. Rev. 1987, 87, 1107-1136. (b) Hecht, S. M. Acc. Chem. Res. 1986, 19, 383-391. Stewart, L. C.; Klinman, J. P. Annu. Rev. Biochem. 1988, 57, 551-592. Tian, G.; Berry, J. A.; Klinman, J. P. Biochemistry 1994, 33, 226-234. (e) Lin, C. H.; Ito, T.; Wang, J.-X.; Lunsford, J. H. J. Am. Chem. Soc. 1987, 109, 4808 and references therein.
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93. (b) For earlier discussions of the formation of organic radicals from diamagnetic precursors, see: Pryor, W. A. in Organic Free Radicals; Pryor, W. A., Ed.; ACS Symposium Series 69; Washington, DC, 1978; pp 33-62;. Harmony, J. A. K. Methods Free-Radical Chem. 1974, 5, 101-176.
94. 3) can be used to understand reactions in toluene solvent in the Polanyi correlations (Figure 5, which also assumes that gas phase RO-H values can be used in the condensed phase).
95. (b) Wayner, D. D. M.; Lusztyk, E.; Page, D.; Ingold, K. U.; Mulder, P.; Laarhoven, L. J. J.; Aldrich, H. S. J. Am. Chem. Soc. 1995, 117, 8737-8744.
96. For leading references, see: (a) Bordwell, F. G.; Cheng, J.-P.; Ji, G.-Z.; Satish, A. V.; Zhang, X. J. Am. Chem. Soc. 1991, 113, 9790-9795. (b) Bordwell, F. G.; Liu, W.-Z. J. Am. Chem. Soc. 1996, 118, 8777-8781. (c) Parker, V. D. J. Am. Chem. Soc. 1992, 114, 7458-7462; correction, 1993, 115, 1201. (d) Tilset, M.; Parker, V. D. J. Am. Chem. Soc. 1989, 111, 6711-6717; correction, 1990, 112, 2843. (e) Reference 60b.
97. For leading references, see: (a) Bordwell, F. G.; Cheng, J.-P.; Ji, G.-Z.; Satish, A. V.; Zhang, X. J. Am. Chem. Soc. 1991, 113, 9790-9795. (b) Bordwell, F. G.; Liu, W.-Z. J. Am. Chem. Soc. 1996, 118, 8777-8781. (c) Parker, V. D. J. Am. Chem. Soc. 1992, 114, 7458-7462; correction, 1993, 115, 1201. (d) Tilset, M.; Parker, V. D. J. Am. Chem. Soc. 1989, 111, 6711-6717; correction, 1990, 112, 2843. (e) Reference 60b.
98. For leading references, see: (a) Bordwell, F. G.; Cheng, J.-P.; Ji, G.-Z.; Satish, A. V.; Zhang, X. J. Am. Chem. Soc. 1991, 113, 9790-9795. (b) Bordwell, F. G.; Liu, W.-Z. J. Am. Chem. Soc. 1996, 118, 8777-8781. (c) Parker, V. D. J. Am. Chem. Soc. 1992, 114, 7458-7462; correction, 1993, 115, 1201. (d) Tilset, M.; Parker, V. D. J. Am. Chem. Soc. 1989, 111, 6711-6717; correction, 1990, 112, 2843. (e) Reference 60b.
99. For leading references, see: (a) Bordwell, F. G.; Cheng, J.-P.; Ji, G.-Z.; Satish, A. V.; Zhang, X. J. Am. Chem. Soc. 1991, 113, 9790-9795. (b) Bordwell, F. G.; Liu, W.-Z. J. Am. Chem. Soc. 1996, 118, 8777-8781. (c) Parker, V. D. J. Am. Chem. Soc. 1992, 114, 7458-7462; correction, 1993, 115, 1201. (d) Tilset, M.; Parker, V. D. J. Am. Chem. Soc. 1989, 111, 6711-6717; correction, 1990, 112, 2843. (e) Reference 60b.
100. For leading references, see: (a) Bordwell, F. G.; Cheng, J.-P.; Ji, G.-Z.; Satish, A. V.; Zhang, X. J. Am. Chem. Soc. 1991, 113, 9790-9795. (b) Bordwell, F. G.; Liu, W.-Z. J. Am. Chem. Soc. 1996, 118, 8777-8781. (c) Parker, V. D. J. Am. Chem. Soc. 1992, 114, 7458-7462; correction, 1993, 115, 1201. (d) Tilset, M.; Parker, V. D. J. Am. Chem. Soc. 1989, 111, 6711-6717; correction, 1990, 112, 2843. (e) Reference 60b.
101. -) = 7.4: Rush, J. D.; Bielski, B. H. Inorg. Chem. 1995, 34, 5832-5838.
102. (b) The previously accepted value of 10.5 was taken from the following: Lister, M. W.; Yoshino, Y. Can. J. Chem. 1960, 38, 2342-2348. Heckner, K.-H.; Landsberg, R. J. Inorg. Nucl. Chem. 1967, 19, 423-430.
103. (b) The previously accepted value of 10.5 was taken from the following: Lister, M. W.; Yoshino, Y. Can. J. Chem. 1960, 38, 2342-2348. Heckner, K.-H.; Landsberg, R. J. Inorg. Nucl. Chem. 1967, 19, 423-430.
104. 2), unit mole fraction instead of 1 M. We thank Professors John Brauman (Stanford) and Neil Bartlett (Berkeley) for bringing this to our attention (personal communications, January 1995).
105. 61-67b
106. JANAF Thermochemical Tables, 3rd ed.; J. Phys. Chem. Ref. Data 1985, 14, Suppl. 1.
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109. -) = 80.7 ± 3 kcal/mol.
110. 3) = 80 ± 2 kcal/mol.
111. (a) D(HO-H) = 119.2 kcal/mol, D(H-Br) = 87.4 kcal/mol, D(HI) = 71.4 kcal/mol derived from data in ref 65.
112. tBuOO-H).
113. Buxton, G. V.; Greenstock, C. L.; Helman, W. P.; Ross, A. B. J. Phys. Chem. Ref. Data 1988, 17, 513.
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120. 71c,f
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123. The detailed interpretation of α in Polanyi and Brønsted relations as indicating the position of the transition state along the reaction coordinate is not thought to be generally applicable: Pross, A. Theoretical and Physical Principles of Organic Reactivity; Wiley: New York, 1995; pp 175-182. Lowry, R. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; Harper & Row: New York, 1987; pp 671 -676 and references therein.
124. The detailed interpretation of α in Polanyi and Brønsted relations as indicating the position of the transition state along the reaction coordinate is not thought to be generally applicable: Pross, A. Theoretical and Physical Principles of Organic Reactivity; Wiley: New York, 1995; pp 175-182. Lowry, R. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; Harper & Row: New York, 1987; pp 671 -676 and references therein.
125. 74c kcal/mol).
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