Synthesis of Heterocyclic Pentavalent Phosphorus Compounds from Phosphite Derivatives and Indane-1,2,3-Trione

Abstract

Reaction of trialkylphosphite derivatives with indane-1,2,3-trione proceeds smoothly at room temperature to afford the corresponding heterocyclic pentavalent [P(V)] phosphorus compounds via an intermolecular [4+1] cycloaddition reaction in excellent yields under solvent-free conditions. We also used dimethylphosphite and diethylphosphite instead of trialkylphosphites in this reaction, but the corresponding pentavalent phosphorus compounds were not isolated, and in both cases phosphate derivatives were obtained. The structures of the products were deduced from their IR, ¹H NMR, ¹³C NMR, and ³¹P NMR spectra, and mass spectrometry.

Keywords:

• Dialkylphosphite
• heterocyclic pentavalent phosphorus compound
• indane-1,2,3-trione
• intermolecular [4+1] cycloaddition reaction
• solvent-free conditions
• stereochemistry
• trialkylphosphite

Acknowledgments

This work was supported by the Zanjan University.