PHOSPHORUS-CONTAINING NUCLEOPHILES IN REACTIONS WITH POLYFLUORINATED ORGANIC-COMPOUNDS

The paper reviews new experimental data on the reactions of phosphorus-containing nucleophiles (triphenylphosphine, trialkylphosphines, trialkylphosphites, hexaethyltriamidophosphite, etc.) with perfluorinated olefins, aromatic and heterocyclic compounds both with and without phosphorus. It has been shown that the reactions of hexaethyltriamidophosphite and trialkylphosphines with polyfluoroaromatic compounds and perfluoroolefins form phosphoranes which decompose with generation of aryl and alkenyl anions. The review discusses new reactions of such anions with C-electrophiles and the compounds containing mobile halogen atoms. Possible pathways of Arbuzov reactions of unsaturated perfluorinated compounds are analyzed. Potential applications of these reactions to organic synthesis are discussed.