Synthesis and nucleophilic substitution of allenyl(m-nitrophenyl)iodanes as a new propynyl cation-equivalent species: synthesis of propynyl ethers, esters, and amides
Abstract
Treatment of diacetoxy(m-nitrophenyl)iodane with propynylsilanes in the presence of BF3·Et2O gives allenyl(m-nitrophenyl)iodanes, which act as propynyl cation-equivalent species and undergo regioselective nucleophilic substitution with alcohols, carboxylic acids and nitriles to give propynyl ethers, esters and amides.