COOXIDATION REACTION IN THE SINGLET OXYGENATION OF CYCLIC AND BENZYLIC SULFIDES - S-HYDROPEROXYSULFONIUM YLIDE INTERMEDIATE AS A NEW EPOXIDIZING SPECIES

被引：40

作者：

AKASAKA, T ^{[1
]}

SAKURAI, A ^{[1
]}

ANDO, W ^{[1
]}

机构：

[1] UNIV TSUKUBA,DEPT CHEM,SAKURA,IBARAKI 305,JAPAN

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1991年 / 113卷 / 07期

关键词：

D O I：

10.1021/ja00007a051

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of singlet oxygen with a series of 3-benzoyl-4-(methoxycarbonyl)thiazolidine derivatives and alkyl benzyl sulfides in methylene chloride in the presence of olefins has been investigated. The reaction of singlet oxygen with the sulfides caused cooxidation of olefins to the corresponding epoxides in substantial yields. The epoxidation of olefins by the active oxidizing species generated in photosensitized oxygenation of the sulfides is provided, suggesting that the new epoxidizing species is probably the S-hydroperoxysulfonium ylide intermediate derived from a persulfoxide intermediate by intramolecular alpha-proton abstraction.

引用

页码：2696 / 2701

页数：6

共 71 条

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