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Volumn 124, Issue 44, 2002, Pages 13185-13193

Remarkably stable iron porphyrins bearing nonheteroatom-stabilized carbene or (alkoxycarbonyl)carbenes: Isolation, X-ray crystal structures, and carbon atom transfer reactions with hydrocarbons

Author keywords

[No Author keywords available]

Indexed keywords

ISOLATION;

EID: 0037032218     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja020391c     Document Type: Article
Times cited : (178)

References (57)
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    • For reviews on iron porphyrin-catalyzed epoxidation or hydroxylation reactions that are generally believed to involve oxoiron porphyrin intermediates, see: (a) Ellis, P. E., Jr.; Lyons, J. E. Coord. Chem. Rev. 1990, 105, 181. (b) Meunier, B. Chem. Rev. 1992, 92, 1411. (c) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404. (d) Mansuy, D. Coord. Chem. Rev. 1993, 125, 129. For examples of observed oxoiron porphyrins and their oxygen atom transfer reactions with hydrocarbons, see: (e) Groves, J. T.; Haushalter, R. C.; Nakamura, M.; Nemo, T. E.; Evans, B. J. J. Am. Chem. Soc. 1981, 103, 2884. (f) Tsuchiya, S. J. Chem. Soc., Chem. Commun. 1991, 716. (g) Yamaguchi, K.; Watanabe, Y.; Morishima, I. J. Chem. Soc., Chem. Commun. 1992, 1721. (h) Fujii, H. J. Am. Chem. Soc. 1993, 115, 4641. (i) Groves, J. T.; Gross, Z.; Stern, M. K. Inorg. Chem. 1994, 33, 5065. (j) Traylor, T. G.; Kim, C.; Richards, J. L.; Xu, F.; Perrin, C. L. J. Am. Chem. Soc. 1995, 117, 3468. (k) Gross, Z.; Nimri, S. J. Am. Chem. Soc. 1995, 117, 8021. (l) Goh, Y. M.; Nam, W. Inorg. Chem. 1999, 38, 914.
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    • This contrasts with the case of non-porphyrin iron carbene complexes, whose carbon atom transfer reactions with alkenes to form cyclopropanes have been investigated extensively. See for example: Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411.
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    • 2-carbide complexes, have also been structurally characterized; see: (a) Goedken, V. L.; Deakin, M. R.; Bottomley, L. A. J. Chem. Soc., Chem. Commun. 1982, 607. (b) Mansuy, D.; Battioni, J. P.; Lavallee, D.; Fischer, J.; Weiss, R. Inorg. Chem. 1988, 27, 1052. (c) Beck, W.; Knauer, W.; Robl, C. Angew. Chem., Int. Ed. Engl. 1990, 29, 318.
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    • 2-carbide complexes, have also been structurally characterized; see: (a) Goedken, V. L.; Deakin, M. R.; Bottomley, L. A. J. Chem. Soc., Chem. Commun. 1982, 607. (b) Mansuy, D.; Battioni, J. P.; Lavallee, D.; Fischer, J.; Weiss, R. Inorg. Chem. 1988, 27, 1052. (c) Beck, W.; Knauer, W.; Robl, C. Angew. Chem., Int. Ed. Engl. 1990, 29, 318.
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    • 2-carbide complexes, have also been structurally characterized; see: (a) Goedken, V. L.; Deakin, M. R.; Bottomley, L. A. J. Chem. Soc., Chem. Commun. 1982, 607. (b) Mansuy, D.; Battioni, J. P.; Lavallee, D.; Fischer, J.; Weiss, R. Inorg. Chem. 1988, 27, 1052. (c) Beck, W.; Knauer, W.; Robl, C. Angew. Chem., Int. Ed. Engl. 1990, 29, 318.
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    • 2]. Only the bis(carbene) complex can undergo carbon atom transfer into the saturated C-H bonds of unfunctionalized alkenes; see: (a) Li, Y.; Huang, J.-S.; Zhou, Z.-Y.; Che, C.-M. J. Am. Chem. Soc. 2001, 123, 4843. (b) Che, C.-M.; Huang, J.-S. Coord. Chem. Rev. 2002, 231, 151.
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    • 2]. Only the bis(carbene) complex can undergo carbon atom transfer into the saturated C-H bonds of unfunctionalized alkenes; see: (a) Li, Y.; Huang, J.-S.; Zhou, Z.-Y.; Che, C.-M. J. Am. Chem. Soc. 2001, 123, 4843. (b) Che, C.-M.; Huang, J.-S. Coord. Chem. Rev. 2002, 231, 151.
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    • 2O} contaminated by [Fe(TPFPP)(OH)].
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    • note
    • The higher reactivity of cumene than that of ethylbenzene toward the C-H insertion reactions might stem from a higher activity of the tertiary benzylic C-H bond in the former than the secondary benzylic C-H bonds in the latter.


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