Ligand Exchange Reaction of Sulfoxides in Organic Synthesis. A Novel Method for Synthesizing Acetylenes from Carbonyl Compounds through β-Trifluoromethanesulfonyloxy Vinyl Sulfoxides
α-Sulfinyl ketones were prepared by the reaction of alkyl phenylsulfoxide or chloromethyl p-tolyl sulfoxide with aldehydes or methyl esters in high yields, and were converted to acetylenes through β-trifluoromethanesulfonyloxy vinyl sulfoxides by the ligand exchange reaction of the sulfinyl group.
Ligand exchange reaction of sulfoxides in organic synthesis: A novel method for synthesizing acetylenes and allenes from carbonyl compounds through sulfoxides having a trifluoro-methanesulfonyloxy group on the β-carbon
A novel method for synthesizing acetylenes and allenes from carbonyl compounds is described. Ligand exchange reaction of alkenylsulfoxides having a trifluoromethanesulfonyloxy group on the β-carbon, which were derived from α-alkyl β-ketosulfoxides, with n-BuLi gave disubstituted acetylenes in good yields. In the case of alkenylsulfoxides having both the trifluoromethanesulfonyloxy and aryl groups on