On the mechanism of nucleophilic substitution of allenyl(aryl)iodine(III): Formation of propargyl cation and competition with sigmatropic rearrangement
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.
Ochiai, Masahito,Kida, Michio,Okuyama, Tadashi
p. 6207 - 6210
(2007/10/03)
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