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Participation of two distinct hydroxylating intermediates in iron(III) porphyrin complex-catalyzed hydroxylation of Alkanes

Title
Participation of two distinct hydroxylating intermediates in iron(III) porphyrin complex-catalyzed hydroxylation of Alkanes
Authors
Nam W.Mi Hee LimSun Kyung MoonKim C.
Ewha Authors
남원우
SCOPUS Author ID
남원우scopus
Issue Date
2000
Journal Title
Journal of the American Chemical Society
ISSN
0002-7863JCR Link
Citation
vol. 122, no. 44, pp. 10805 - 10809
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
We have obtained evidence that acylperoxo-iron(III) porphyrin complexes 1a are involved as reactive hydroxylating intermediates in the hydroxylation of alkanes by m-chloroperoxybenzoic acid (m-CPBA) catalyzed by electron-deficient iron(III) porphyrin complexes containing chloride as an anionic axial ligand in a solvent mixture of CH2Cl2 and CH3CN at -40 °C. In addition to the intermediacy of 1a, oxoiron(IV) porphyrin cation radical complexes 2 are formed as the reactive hydroxylating intermediates in the alkane hydroxylations by m-CPBA catalyzed by the iron(III) porphyrin complexes containing triflate (CF3SO3 -) as an anionic axial ligand under the same reaction conditions. In line with the recent proposal by Newcomb, Coon, Vaz, and co-workers for cytochrome P-450 reactions, these results suggest that two distinct electrophilic oxidants such as 1a and 2 effect the alkane hydroxylations in iron porphyrin models, depending on the reaction conditions such as the nature of the anionic axial ligands of iron(III) porphyrin complexes.
DOI
10.1021/ja0010554
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자연과학대학 > 화학·나노과학전공 > Journal papers
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