Reaction of Sodium Diethylnitroxide with ‎Fluorobenzenes, Pentafluoropyridine and ‎Halogenopyridines

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Journal Title, Volume, Page: 
Journal of Fluorine Chemistry Volume 44, Issue 3, Pages 441–444
Year of Publication: 
1989
Authors: 
Waheed Jondi
Department of Chemistry, The University of Manchester Institute of Science and Technology, Manchester M60 1QD U.K
Current Affiliation: 
Department of Chemistry, Faculty of Science, An-Najah National University, Nablus, Palestine
Ronald Eric Banks
Department of Chemistry, The University of Manchester Institute of Science and Technology, Manchester M60 1QD U.K
Anthony Edgar Tipping
Department of Chemistry, The University of Manchester Institute of Science and Technology, Manchester M60 1QD U.K
Preferred Abstract (Original): 

Treatment of pentafluoropyridine with sodium diethylnitroxide in diethyl ether gave tetrafluoropyridines 4-RC5F4N(R = ONEt2, NEt2, NHEt and O H2View the MathML sourceEt2); in the presence of View the MathML source-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-OH2View the MathML sourceEt2 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.