A CONVENIENT SYNTHESIS OF PERFLUOROALKYLATED HYDROXY- AND DIHYDROXYPHOSPHONATES

Perfluoroalkylated 1-hydroxyphosphonates may be easily synthesized in good yield by the reaction of the corresponding perfluoroalkyl aldehyd es with dimethyl phosphite. Perfluoroalkylcarboxylic esters react with the phosphonate anion to give (perfluoroacyl)methylphosphonates, thei r tautomeric isomers (2-perfluoroalkyl-2-hydroxy)vinylphosphonates and their hydrates (2-perfluoroalkyl-2,2-dihydroxy)ethylphosphonates, whi ch are reduced with sodium borohydride affording perfluoroalkylated 2- hydroxyphosphonates in 61-68% yield. Perfluoroalkylated dihydroxyphosp honates may be obtained by the reaction of the bisphosphonate anion wi th perfluoroalkyl aldehydes followed by oxidation with osmium tetraoxi de in 54-68% yield.