Oxidation of perfluoronaphthols by lead tetraacetate and lead dioxide

Depending on the reaction conditions, oxidation of perfluoronaphthols by Pb(OAc)₄ proceeds by two routes. Under mild conditions (20°C) oxidation leads to the products of dimerisation of perfluoronaphthoxy radicals. At a higher temperature (80°C) the reaction leads to acetoxydienones. The mechanistic aspects of oxidation of perfluoronaphthols by Pb(OAc)₄ are discussed.