Reductive condensation of trichloromethylarenes with hydroxylamine and hydrazines in pyridine

Article abstract of DOI:10.1016/S0040-4020(01)90502-2

The interaction of trichloromethylarenes with hydroxylamine in pyridine involves the reductive oximation of aryltrichloromethanes. Further transformations of the oximes in the reaction course can result in the formation of nitriles or 3,5-diaryl-1,2,4-oxadiazoles as final products. The conversion depth depends on reaction conditions and structures of trichloromethyl-arenes. When hydrazines used instead of hydroxylamine, respectivebenzaldehyde hydrazones or azines are obtained.