A novel effective electrophile: β-trifluoroacetylketene diphenyldithioacetal S,S-tetroxide

Article abstract of DOI:10.1016/j.tetlet.2003.12.022

A synthesis of a novel electrophilic reagent - β- trifluoroacetylketene diphenyldithioacetal S,S-tetroxide 3 is described. The reaction of 3 with various electron-rich aromatics such as 1,3-dimethoxybenzene, 2-methylthiophene, N-methylpyrrole, and 2-methylindole was investigated. In the course of these reactions an unusual migration of a phenylsulfonyl group takes place. An easy and ready for scale-up procedure for the synthesis of previously unknown β-aryl, α-phenylsulphonyl substituted α,β-unsaturated trifluoromethyl ketones is reported.