期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 77, 期 7, 页码 3508-3517出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo300313v
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资金
- Natural Sciences and Engineering Research Council (NSERC) of Canada
- Province of Alberta
- Alberta Innovates-Health Solutions
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.
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