Polyfluoroarenes. Part XIV. Synthesis of halogenophthalocyanines

Tetrafluorophthalonitrile reacts with a variety of metals and metal halides to give halogenophthalocyanines. The reaction with zinc, zinc bromide, or zinc iodide gives zinc hexadecafluorophthalocyanine in good yield, but zinc chloride, iron(III) chloride, and aluminium chloride react to give mixtures of polychloropolyfluorophthalocyanines. Copper(II) hexadecafluorophthalocyanine may be obtained from the reaction of copper, copper(I) chloride, or copper(II) chloride with tetrafluorophthalonitrile, and a similar reaction with tin(II) chloride yields dichlorotin(IV) hexadecafluorophthalocyanine. A new route to zinc phthalocyanine itself and the first syntheses of zinc hexadecachlorophthalocyanine and chloroiron(III) hexadecachlorophthalocyanine are described.