Cyclic seleninate esters as catalysts for the oxidation of sulfides to sulfoxides, epoxidation of alkenes, and conversion of enamines to α-hydroxyketones

EA Mercier, CD Smith, M Parvez…

Index: Mercier, Eric A.; Smith, Chris D.; Parvez, Masood; Back, Thomas G. Journal of Organic Chemistry, 2012 , vol. 77, # 7 p. 3508 - 3517

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Citation Number: 27

Abstract

Cyclic seleninate esters serve as catalysts for the rapid oxidation of sulfides to sulfoxides, alkenes to epoxides, and enamines to α-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 ...