On the mechanism of nucleophilic substitution of allenyl(aryl)iodine(III): Formation of propargyl cation and competition with sigmatropic rearrangement

Article abstract of DOI:10.1016/S0040-4039(98)01276-3

The ratios of nucleophilic substitution versus [3,3] sigmatropic rearrangement for the collapse of allenyl(aryl)-iodine(III), generated from the reaction of aryliodanes with propargylsilanes in the presence of BF₃- Et₂O in alcohols, were determined. A proposed mechanism involves generation of propargyl cations from the allenyliodine(III) via a unimolecular pathway.