N-FLUORO-COMPOUNDS .3. SOME FREE-RADICAL REACTIONS OF PERFLUORO-N-FLUOROPIPERIDINE

U.v. Irradiation of perfluoro-N-fluoropiperidine yields, inter alia, perfluoro-NN′-bipiperidyl. This product is also obtained, together with perfluorobicyclobutyl and perfluoro-(N-cyclobutylpiperidine), when the N-fluoropiperidine is irradiated in the presence of perfluorocyclobutene. Irradiation of perfluoro-N-fluoropiperidine in the presence of oxygen gives a product that decomposes to perfluoropentamethylene nitroxide when heated. Reaction of the nitroxide with iron, nitric oxide, or polystyrene yields perfluoro-2,3,4,5-tetrahydropyridine, perfluoro-O- nitrosopentamethylenehydroxylamine, and perfluoropentamethylenehydroxylamine, respectively. Pyrolysis of perfluoro-(N-cyclobutylpiperidine) gives perfluoro-(N-vinylpiperidine).