Halides-based electrophiles mediated epoxide ring-opening reactions of α,β-epoxysulfoxides in C6-series : Deoxygenation versus dehydration and an overall 1,2-keto transposition

Article abstract of DOI:10.1016/S0040-4020(01)80698-0

New syntheses of α-thiosubstituted carbonyl compounds with the carbonyl carbon being the one that originally does not carry the sulfoxide group from six-membered ring α,β-epoxysulfoxides and several halides-based electrophiles are described. Mechanistic considerations for deoxygenation as well as dehydration reactions are also discussed. In addition, methodology for achieving 1,2-carbonyl transposition starting with isomerically pure cyclohexenyl sulfides derived from isophorone and cholestan-3-one is briefly reported.