SELECTIVE ORTHO-ARYLATION OF POLYFLUORINATED HYDROXYAROMATIC COMPOUNDS WITH LEAD ARYL ACETATES

Reactions of salts of pentafluorophenol and heptafluoronaphthols with lead aryl acetates have led to the formation of arylcyclohexadienones with an ortho-quinoid structure. The arylation of sodium pentafluoroph enoxide and heptafluoro-2-naphthoxide is accompanied by nucleophilic s ubstitution of fluorine at a double bond by pentafluorophenoxy and hep tafluoro-2-naphthoxy groups, respectively. Reduction of the resulting arylcyclohexadienones gave polyfluorinated phenols and naphthols with aryl and hydroxy groups in the 1,2-position.