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

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
39
Issue
34
Identifiers
DOI: 10.1016/s0040-4039(98)01276-3
Keywords
  • Hypervalent Elements
  • Carbenium Ions
  • Substitution
  • Rearrangements

Abstract

Abstract 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 BF 3Et 2O in alcohols, were determined. A proposed mechanism involves generation of propargyl cations from the allenyliodine(III) via a unimolecular pathway.

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