63489-56-5Relevant articles and documents
Selective mono-and diamination of polyfluorinated benzenes and pyridines with liquid ammonia
Vaganova,Kusov,Rodionov,Shundrina,Malykhin
, p. 2239 - 2246 (2008/09/20)
Amination of pentafluoropyridine, 2,3,5,6-tetrafluoropyridine, 4-chlorotetrafluoropyridine, 3,5-dichlorotrifluoropyridine, octafluorotoluene, α,α,α,2,3,5,6-heptafluorotoluene, decafluoro-m-xylene, decafluorobiphenyl, hexafluorobenzene, and pentafluorobenzene with liquid ammonia was investigated. Bis-aminodefluorination temperatures for the majority of substrates were shown to exceed significantly the corresponding temperatures of monoaminodefluorination. The optimal conditions for selective preparation of mono-and diaminopolyfluoro(het)arenes were elucidated. An efficient method for isolation of particular polyfluorophenylenediamines from product mixtures formed in nonselective reactions of pentafluorobenzene and hexafluorobenzene with aqueous ammonia based on complexation with a crown ether is proposed.
N-Halogeno-compounds. Part 7. Synthesis and Iodine-catalysed Rearrangement to 6-Chloroimino-1-azacyclohexadienes of 4-Substituted 2-(Dichloroamino)-3,5,6-trifluoropyridines
Banks, Ronald, E.,Barlow, Michael G.,Hornby, John C.,Mamaghani, Manouchehr
, p. 817 - 821 (2007/10/02)
Electrophilic chlorination of the fluorinated 2-aminopyridines 4-X*C5F3N*NH2-2 with t-butyl hypochlorite gave the 2-(dichloroamino)-compounds 4-X*C5F3N*NCl2-2; these isomerized to mixtures of the corresponding 3-chloro-6-chloroimino-1-azacyclohexa-1,4- (predominantly) and 5-chloro-6-chloroimino-1-azacyclohexa-1,3-dienes when treated with iodine. 'Spontaneous' formation of 3-chloro-6-chloroimino-2,3,5-trifluoro-4-methyl-1-azacyclohexa-1,4-diene occurred following chlorination (ButOCl) of 2-amino-3,5,6-trifluoro-4-methylpyridine. 3-Chloro-6-chloroimino- 3,5-difluoro-4-X-2-oxo-1-azacyclohex-4-enes (X = H, Me, or Cl) were obtained by displacement of fluorine from the corresponding 3-chloro-6-chloroimino-2,3,5-trifluoro-1-azacyclohexa-1,4-dienes with water; hydrolysis of 4,5-dichloro-6-chloroimino-2,3,5-trifluoro-1-azacyclohexa-1,3-diene provided 4,5-dichloro-6-chloroimino-3,5-difluoro-2-oxo-1-azacyclohex-3-ene.Pyrolysis of the 2-(dichloroamino)pyridines 4-X*C5F3N*NCl2-2 gave the azo-compounds 2,2'-2.The 19F n.m.r. spectra of the chloroimino-1-azacyclohexadienes have been analysed.