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Mechanistic insight into the aromatic hydroxylation by high-valent iron(IV)-oxo porphyrin π-cation radical complexes

Title
Mechanistic insight into the aromatic hydroxylation by high-valent iron(IV)-oxo porphyrin π-cation radical complexes
Authors
Kang M.-J.Woon J.S.Han A.-R.Choi Y.S.Jang H.G.Nam W.
Ewha Authors
남원우
SCOPUS Author ID
남원우scopus
Issue Date
2007
Journal Title
Journal of Organic Chemistry
ISSN
0022-3263JCR Link
Citation
vol. 72, no. 16, pp. 6301 - 6304
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
(Chemical Equation Presented) Mechanistic studies of the aromatic hydroxylation by high-valent iron(IV)-oxo porphyrin π-cation radicals revealed that the aromatic oxidation involves an initial electrophilic attack on the π-system of the aromatic ring to produce a tetrahedral radical or cationic σ-complex. The mechanism was proposed on the basis of experimental results such as a large negative Hammett ρ 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. © 2007 American Chemical Society.
DOI
10.1021/jo070557y
Appears in Collections:
자연과학대학 > 화학·나노과학전공 > Journal papers
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