Vinyltriphenylphosphonium Salt-Mediated Preparation of Fully Substituted Furans and Electron-Poor Imides from Benzoic acid, Cyclohexyl Isocyanide, and Acetylenic Esters

Abstract

Protonation of the reactive intermediates produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates by benzoic acid leads to vinyltriphenylphosphonium salts, which undergo complex reactions with cyclohexyl isocyanide to produce corresponding densely functionalized furans and imides in fairly good yields in neutral conditions. The formulas of the products were deduced from their IR, ¹H NMR, and ¹³C NMR spectra. The reaction is completely stereoselective.

Keywords:

• Acetylenic ester
• densely functionalized furan
• electron-poor imide
• phosphorus ylide
• triphenylphosphine

Acknowledgments

This work was supported by the Zanjan University.