Dipotassium Hydrogen Phosphate Powder Catalyzed Synthesis of Alkyl 2-(2-Alkoxy-2-oxoethyl)dinaphtho[2,1-d:1,2-f][1,3]-dioxepin-2-Carboxylates from Stabilized Phosphorus Ylides in Solvent-Free Conditions

Abstract

The protonation of the highly reactive 1:1 intermediates, produced in the reaction of triphenylphosphine and dialkyl acetylenedicarboxylates, by 1,1-binaphthyl-2,2′-diol leads to vinyltriphenylphosphonium salts, which undergo a Michael addition reaction to produce the corresponding stabilized phosphonium ylides. Dipotassium hydrogen phosphate powder was found to catalyze the conversion of the stabilized phosphonium ylides to alkyl 2-(2-alkoxy-2-oxoethyl)dinaphtho[2,1-d:1,2-f][1,3]-dioxepin-2-carboxylates under solvent-free conditions using microwave (0.6 KW, 3 min) and thermal (100°C, 60 min) conditions.

Keywords:

• 1,1-binaphthyl-2,2′-diol
• dipotassium hydrogen phosphate
• Michael addition
• acetylenic esters
• vinyltriphenylphosphonium salt
• microwave irradiation

Acknowledgments

This work was supported by Zanjan University, Zanjan, Iran.