Origin of the oxygen atom in C-H bond oxidations catalyzed by a water-soluble metalloporphyrin

被引：38
作者：
Balahura, RJ
Sorokin, A
Bernadou, J
Meunier, B
机构：
[1] CNRS,CHIM COORDINAT LAB,F-31077 TOULOUSE 4,FRANCE
[2] UNIV GUELPH,DEPT CHEM,GUELPH,ON N1G 2W1,CANADA
来源：
INORGANIC CHEMISTRY | 1997年 / 36卷 / 16期
关键词：
D O I：
10.1021/ic9700765
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The monopersulfate oxidation of 4-isopropylbenzoic acid performed in (H2O)-O-18 and catalyzed by a water-soluble metalloporphyrin indicated that half of the oxygen atoms incorporated in 4-(1-hydroxy-1-methylethyl)benzoic acid, the primary hydroxylation product, came from water. A redox tautomerism of the active high-valent hydroxo-metal-oxo porphyrin intermediate coupled with an oxygen rebound mechanism explained this result. Under similar conditions, ketoprofen was directly oxidized to 3-benzoylacetophenone, via at least two different reaction pathways. Trapping of radical intermediates by molecular oxygen competed with the oxygen rebound mechanism.
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收藏
页码：3488 / 3492
页数：5
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