✦ LIBER ✦
On the mechanism of nucleophilic substitution of allenyl(aryl)iodine(III): Formation of propargyl cation and competition with sigmatropic rearrangement
✍ Scribed by Masahito Ochiai; Michio Kida; Tadashi Okuyama
- Publisher
- Elsevier Science
- Year
- 1998
- Tongue
- French
- Weight
- 238 KB
- Volume
- 39
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
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-Et20 in alcohols, were determined. A proposed mechanism involves generation of propargyl cations from the allenyliodine(III) via a unimolecular pathway.