Treatment of pentafluoropyridine with sodium diethylnitroxide in diethyl ether gave tetrafluoropyridines 4-RC₅F₄N(R = ONEt₂, NEt₂, NHEt and O⁻ H₂Et₂); in the presence of -dinitrobenzene only the hydroxylamine (R = ONEt₂) was detected. Octafluorotoluene afforded analogous products with the exception of the amine 4- CF₃-C₆F₄-NEt₂, while from the pentafluorobenzene reaction only the salt 4-H- C₆F₄-O⁻H₂Et₂ was isolated. In contrast the reactions involving 2-chloro-3-nitro- and 2-chloro-5-nitro-pyridine yielded the 2-diethylamino derivatives and bis(pyridy)amines.