Fluorocarbon derivatives of nitrogen. Part 5. Replacement of imidoyl halogen by the bistrifluoromethylamino-oxy group: reactions of perfluoro-2-azapropene and related compounds with bis(bistrifluoro-methylamino-oxy)mercury(II) or NN-bistrifluoromethylhydroxylamine–caesium fluoride

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Abstract
Treatment of perfluoro-2-azapropene with bis(bistrifluoromethylamino-oxy)mercury(II) yields the new mercurial {[(CF3)2NOCF2](CF3)N}2Hg (11), chlorinolysis of which provides the N-chloroamine CF3NCICF2ON(CF3)2(16); pyrolysis of the mercurial (11) gives a complex mixture containing the imine CF3NCFON(CF3)2(12) and material tentatively identified as {CF3NC[ON(CF3)2]}2O. The N-chloro-compound (16) reacts with hydrogen chloride and silver cyanide to provide the corresponding amine CF3NHCF2ON(CF3)2 and the related imine (12). The latter product, together with the di-substituted analogue (CF3)2NCF2NCFON(CF3)2, can also be procured by treating perfluoro-2-azapropene with a caesium fluoride–NN-bistrifluoromethylhydroxylamine adduct. This reagent also attacks perfluoro-1-azacyclohexene to yield perfluoro-[2-(dimethylamino-oxy)-1-azacyclohexene] and perfluoro-[2,6-bis(dimethylamino-oxy)-1-azacyclohexene], and similarly effects nucleophilic substitution in pentafluoro-pyridine to provide 4-(bistrifluoromethylamino-oxy)-2,3,5,6-tetrafluoropyridine. The mercurial [(CF3)2NO]2Hg attacks the alkyliminocarbonyl chloride Me3CNCCl2 to give the bistrifluoromethylamino-oxy-derivatives Me3CNCCl[ON(CF3)2] and Me3CNC[ON(CF3)2]2.
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