Metalloporphyrin-catalyzed oxidation of 2-methylnaphthalene to vitamin K-3 and 6-methyl-1,4-naphthoquinone by potassium monopersulfate in aqueous solution

被引：110

作者：

Song, R ^{[1
]}

Sorokin, A ^{[1
]}

Bernadou, J ^{[1
]}

Meunier, B ^{[1
]}

机构：

[1] CNRS,CHIM COORDINAT LAB,F-31077 TOULOUSE 4,FRANCE

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 03期

关键词：

D O I：

10.1021/jo961421v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The metalloporphyrin-catalyzed oxidation of 2-methynaphthalene (1) by potassium monopersulfate produced mainly two naphthoquinones: 2-methyl-1,4-naphthoquinone (2) (menadione or vitamin K-3) and 6-methyl-1,4-naphthoquinone (3). In aqueous solution and at room temperature in the presence of 5 mol % of the water-soluble metalloporphyrins MnTPPS or FeTMPS, 2-methylnaphthalene was quantitatively oxidized to quinones 2 and 3. Based on experiments performed in O-18-labeled water and according to the ''redox tautomerism'' mechanism previously described for such catalysts, the oxidation to quinones is proposed to be mainly due to a cytochrome P-450-type oxygenation reaction (oxygen atom transfer),rather than a peroxidase-type oxidation (electron transfer).

引用

页码：673 / 678

页数：6