Cyclic Seleninate Esters as Catalysts for the Oxidation of Sulfides to Sulfoxides, Epoxidation of Alkenes, and Conversion of Enamines to α-Hydroxyketones

被引：45
|
作者：
Mercier, Eric A. [1 ]
Smith, Chris D. [1 ]
Parvez, Masood [1 ]
Back, Thomas G. [1 ]
机构：
[1] Univ Calgary, Dept Chem, Calgary, AB T2N 1N4, Canada
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 07期
基金：
加拿大自然科学与工程研究理事会;
关键词：
AQUEOUS HYDROGEN-PEROXIDE; BAEYER-VILLIGER OXIDATION; BENZENESELENINIC ANHYDRIDE; CARBONYL-COMPOUNDS; DIPHENYLSELENINIC ANHYDRIDE; N-SULFONYLOXAZIRIDINES; ANGULAR HYDROXYLATION; HOMOGENEOUS SOLUTION; DIPHENYL DISELENIDE; BUTYL HYDROPEROXIDE;
D O I：
10.1021/jo300313v
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Cyclic seleninate esters serve as catalysts for the rapid oxidation of sulfides to sulfoxides, alkenes to epoxides, and enamines to alpha-hydroxyketones. Optimal conditions were found that minimize the overoxidation of the product sulfoxides to sulfones and the hydrolysis of epoxides to diols. In some examples such as styrene derivatives, oxidative cleavage was observed instead of epoxidation. The enamine oxidations proceed via the initial formation of dimeric 2,5-diamino-1,4-dioxane species, which were hydrolyzed in situ to the final products. The structure of one such dimer was confirmed by X-ray crystallography.
引用
收藏
页码：3508 / 3517
页数：10
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