Synthesis of oligophosphonate aromatic systems using the Michaelis-Arbuzov reaction and microwave radiation

Abstract

The microwave-assisted Michaelis-Arbuzov reaction of 2-aryloxy-1,3,2-dioxaphosphinanes was investigated. The dioxaphosphinane groups immobilized on dinaphthylmethane or resorcinarene core react with alkyl/arylalkyl halides/bromoethyl acetate with opening of the phosphinane ring to give linear unsymmetrical phosphonates. The number and spatial orientation of the resulting phosphonate groups depend on the structure and topology of the aromatic substrate and the nature of the alkylating reagent.

Graphical Abstract

Keywords:

• 2-Aryloxy-1,3,2-dioxaphosphinanes
• dinaphthylmethanes
• resorcinarenes
• Michaelis-Arbuzov reaction
• phosphonates
• alkyl/arylalkyl halides/bromoethyl acetate

Acknowledgement

This work was financially supported by the Russian Foundation for Basic Research (project no. 18-03-00347a).