91299-16-0Relevant articles and documents
A Novel Synthesis of Diareno-1,2-diazepines: Intramolecular Dehydrofluorination of 2,4,6-Trimethylphenylazo-derivatives of Fluoroaromatic Compounds
Alty, Adam C.,Banks, Ronald E.,Fishwick, Brian R.,Pritchard, Robin G.,Thompson, A. Ronald
, p. 832 - 833 (1984)
Formation of 1,2-diazepines via intramolecular elimination of hydrogen fluoride derived from methyl and fluorine substituents lying ortho to N=N linkages occurs when the azo-compounds 2,4,6-Me3C6H2N=NC6F5, 2,4,6-Me3C6H2N=NC6F4CF3-4, and 4-(2,4,6-Me3C6H2N=
Fluorinated biphenyls from aromatic arylations with pentafluorobenzenediazonium and related cations. Competition between arylation and azo coupling
Kosynkin, Dmitry,Bockman, T. Michael,Kochi, Jay K.
, p. 2003 - 2012 (2007/10/03)
High yields of the mixed perfluorinated biaryls (C6F5-Ar) are obtained by the catalytic dediazonlatlon of the pentafluorobenzenediazonium salt (C6F5N2+BF4-) in acetonitrile solutions containing various aromatic substrates (ArH) together with small amounts of iodide salts. Activated (electron-rich) as well as deactivated (electron-poor) arenes are successfully pentafluorophenylated by this method. The arylation is distinct from the azo coupling of the same substrates, which takes place in the absence of the iodide catalyst and yields the corresponding diazene (C6F5N=N-Ar) as product. The catalytic role of iodide, and the isomeric product distributions obtained with this procedure indicate that the arylation proceeds via the pentafluorophenyl radical in a efficient homolytic chain process. Since azo coupling involves electrophilic aromatic substitution of electron-rich ArH by C6F5N2+, the two competing pathways are distinct and do not have reactive intermediates in common.
FLUOROCARBON DERIVATIVES OF NITROGEN. PART 16. SYNTHESIS OF SOME UNSYMMETRICAL AROMATIC AZO-COMPOUNDS via DIAZOTISATION OF FLUORINATED ARYL- AND N-HETEROARYL-AMINES IN HYDROFLUORIC OR SULPHURIC ACID
Alty, Adam C.,Banks, Ronald E.,Thompson, A. Ronald,Vellis, Haralambos S.,Fishwick Brian R.
, p. 147 - 170 (2007/10/02)
Coupling reactions of the type ArFN2+ + ArH -> ArFN=NAr + H+ have been accomplished between fluorinated arenediazonium ions selected from the benzenic, pyridinic and pyrimidinic classes F = C6F5, 4-CF3C6F4, 4-C5F4N, 4-C5F3N.Cl-3, 4-C5F2N.Cl2-3,5, 2-C5F3N.CF(CF3)2-4, 4-C4F3N2> and one or more aromatic compounds activated towards electrophilic attack (ArH = 1,3,5-Me3C6H3, 1,3,5-Et3C6H3, MeOC6H5, Me2NC6H5, and naphth-2-ol).The diazonium ions were generated by addition of solid sodium nitrite to solutions of the amines ArFNH2 in anhydrous hydrogen fluoride, 80percent hydrofluoric acid, or 98 percent sulphuric acid mixed with glacial aceticacid and propionic acid.This work has established that perfluorinated arenediazonium ions rank amongst the most electrophilic species of their general class.
Diazotization of pentafluoroaniline by means of anion-catalyzed phase transfer catalysis in a hydrophobic organic solvent
Iwamoto, Hidetoshi,Sonoda, Takaaki,Kobayashi, Hiroshi
, p. 535 - 537 (2007/10/02)
Anion-catalyzed phase-transfer catalysis was successfully applied to diazotization of pentafluoroaniline in a dichloromethane-aqueous sulfuric acid two-phase system.The resulting diazonium group was coupled in situ with anisole, 1-methoxynaphthalene, and mesitylene, and replaced in situ with bromo, hydryl, and phenyl substituents under a two-phase condition.
