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Synthesis of Electron-Poor O -Vinyl Ethers from Stabilized Phosphorus Ylides in the Presence of Dipotassium Hydrogen Phosphate Powder in Solvent-Free Conditions

Protonation of highly reactive 1:1 intermediates, produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates, by phenols leads to vinyltriphenylphosphonium salts, which undergo Michael addition reaction with a conjugate base to produce corresponding stabilized phosphorus ylides. Dipotassium hydrogen phosphate powder was found to catalyze the conversion of stabilized phosphorus ylides to electron-poor O-vinyl ethers in solvent-free conditions under microwave (0.6 KW, 3 min) and thermal (100 °C, 60 min) conditions. Relative population of E and Z isomers of electron-poor O-vinyl ethers was determined via their 1 H NMR spectra.