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Mechanistic insight into the aromatic hydroxylation by high-valent Iron(IV)-oxo porphyrin π-cation radical complexes
Cited 60 time in
Web of Science
Cited 63 time in Scopus
- Authors
- Issue Date
- 2007-08
- Publisher
- AMER CHEMICAL SOC
- Citation
- JOURNAL OF ORGANIC CHEMISTRY, Vol.72 No.16, pp.6301-6304
- Abstract
- [GRAPHICS] Mechanistic studies of the aromatic hydroxylation by high-valent iron(IV)-oxo porphyrin pi-cation radicals revealed that the aromatic oxidation involves an initial electrophilic attack on the pi-system of the aromatic ring to produce a tetrahedral radical or cationic sigma-complex. The mechanism was proposed on the basis of experimental results such as a large negative Hammett rho value and an inverse kinetic isotope effect. By carrying out isotope labeling studies, the oxygen in oxygenated products was found to derive from the iron-oxo porphyrin intermediates.
- ISSN
- 0022-3263
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