The synthesis and reactivity of propargylic trifluoromethanesulfinates unde
r 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 nucleophil
ic addition of the solvent to the allenyl sulfone under the latter conditio
ns has also been observed. (C) 2001 Elsevier Science Ltd. All rights reserv
ed.