Heterocyclic polyfluoro-compounds. Part 40. Preparation of polyfluoroazepines

Abstract

The hexafluoro-Dewar-benzene adduct of phenyl azide yields hexafluoro-1-phenyl-1H-azepine on pyrolysis. Reaction of ethyl azidoformate with hexafluorobenzene yields ethyl hexafluoro-1H-azepine-1-carboxylate (21%), with octafluoronaphthalene yields 1,2-(ethoxycarbonylimino)-1,2,3,4,5,6,7,8-octafluoro-1,2-dihydronaphthalene (23%), and with 1,2,3,4-tetrafluoronaphthalene yields 1,2-(ethoxycarbonylimino)-1,2,3,4-tetrafluoro-1-1,2-dihydronaphthalene (18%) and ethyl 5,6,7,8-tetrafluoro-1-naphthylcarbamate (48%). No azepines were obtained from the reaction of cyanogen azide with the two naphthalenes.