Diels–Alder Cycloadditions of 1,2-Dihydrophosphinine Oxides and Fragmentation-Related Phosphorylations with 2-Phosphabicyclo[2.2.2]Octadiene Oxides Under Green Chemical Conditions—The Role of Microwave and Ionic Liquids

Abstract

The effect of the use of microwave (MW) and solvents including ionic liquids on the Diels–Alder reaction of 1,2-dihydrophosphinine oxides (1) and fragmentation-related phosphorylation of phenols with 2-phosphabicyclo[2.2.2]octadiene oxides (4) was studied. The MW-assisted Diels–Alder reaction of dihydrophosphinine oxides (1) with N-phenylmaleimide may be advantageous to carry out in [bmim][BF₄] due to shorter reaction times, but the dimerization of the double-bond isomers (A and B) of the dihydrophosphinine oxides (1) may be best accomplished under MW in the absence of any solvent. The fragmentation-related phosphorylations may also be carried out under MW, which with the P-phenyl precursor (4a) became more efficient in [bmim][BF₄].

GRAPHICAL ABSTRACT

Keywords:

• Microwave
• ionic liquid
• P-heterocycles
• Diels–Alder reaction
• fragmentation-related phosphorylation

Acknowledgments

This work is connected to the scientific program of the “Development of quality-oriented and harmonized R+D+I strategy and functional model at BME” project. This project is supported by the New Hungary Development Plan (Project ID: TÁMOP-4.2.1/B-09/1/KMR-2010-0002) and also supported by the Hungarian Scientific Research Fund (OTKA K83118).