Abstract Addition of oxygen containing radicals (HO·, t-BuO·, C 6 F 5 COO·, C 6 F 5 SO· 2) to octafluoronaphthalene occurs mainly in the 1-position. The radical intermediates are stabilised by formation of heptafluoronaphthoxyl radical, further transformations of which lead mainly to polyfluorinated derivatives of 1-oxodihydronaphthalenes and 1, 4- naphthoquinone. Reactions with HO· may involve aromatic ring cleavage both in ...