Reaction of Sodium Diethylnitroxide with Fluorobenzenes, Pentafluoropyridine and Halogenopyridines
Ronald Eric Banks
Anthony Edgar Tipping
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.
Journal of Fluorine Chemistry Volume 44, Issue 3, Pages 441–444