title: Cyclic seleninate esters as catalysts for the oxidation of sulfides to sulfoxides, epoxidation of alkenes, and conversion of enamines to α-hydroxyketones.
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 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.
authors.affiliation: Department of Chemistry, University of Calgary, Calgary, Alberta, Canada.
authors.forename: Eric A
authors.initials: EA
authors.lastname: Mercier
authors.forename: Chris D
authors.initials: CD
authors.lastname: Smith
authors.forename: Masood
authors.initials: M
authors.lastname: Parvez
authors.forename: Thomas G
authors.initials: TG
authors.lastname: Back
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001713:Biphenyl Compounds / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D004852:Epoxy Compounds / Q000737:chemistry*; D004952:Esters; D007093:Imidazoles / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013440:Sulfides / Q000737:chemistry*; D013454:Sulfoxides / Q000737:chemistry*
chemical_list: D000475:Alkenes; D001713:Biphenyl Compounds; D004852:Epoxy Compounds; D004952:Esters; D007093:Imidazoles; D007659:Ketones; D013440:Sulfides; D013454:Sulfoxides