view:20506 Last Update: 2019-1-30
Ali Ramazani; Abbas Azizian; Maryam Bandpey; Nader Noshiranzadeh |
One-Step Synthesis of Electron-Poor Alkenes from Triphenylphosphine, Acetylenic Esters, 2,2,2-Trichloroethanol, and Ninhydrin
Protonation of the highly reactive 1:1 intermediates, produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates, by 2,2,2- trichloroethanol leads to vinyltriphenylphosphonium salts, which undergo a Michael addition reaction with a conjugate base to produce the corresponding chlorine-containing stabilized phosphorus ylides. An intermolecular Wittig reaction of the chlorine-containing stabilized phosphorus ylides with ninhydrin leads to the corresponding highly electron-poor chlorine-containing alkenes.