Facile synthesis and rearrangement of propargylic trifluoromethanesulfinates

The synthesis and reactivity of propargylic trifluoromethanesulfinates under various conditions have been investigated. These esters readily undergo [2,3]-sigmatropic rearrangement to the corresponding allenyl trifluoromethyl sulfones, even under solvolytic conditions. An unusually facile nucleophilic addition of the solvent to the allenyl sulfone under the latter conditions has also been observed.