Microwave-Induced Conversion of Stabilized Phosphorus Ylides to Electron-Poor 2H-Cheromenes in the Presence of Silica Gel Powder in Solvent-Free Conditions

Abstract

Protonation of the highly reactive 1:1 intermediates, produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates, by cyclohexan1,3-diones leads to vinyltriphenylphosphonium salts, which undergo a Michael addition reaction with a conjugate base to produce stabilized phosphorus ylides. Silica-gel powder was found to catalyze the conversion of the stabilized phosphorus ylides to corresponding electron-poor 2H-chromenes under solvent-free conditions under microwave irradiation (0.72 KW, 9 min) or thermal conditions (95°C, 45 min) in fairly good yields.

Keywords:

• Acetylenic esters
• cyclohexan-1,3-diones
• microwave irradiation
• silica gel
• vinyltriphenylphosphonium salt

Acknowledgments

This work was supported by the Sandoogh Hemayate as Pajuoheshgharane Keshvare Iran via the research project number N 84114.