75723-76-1Relevant articles and documents
Regiochemistry of nucleophilic substitution of pentachloropyridine with N and O bidentate nucleophiles
Poorfreidoni, Alireza,Ranjbar-Karimi, Reza,Kia, Reza
, p. 4398 - 4406 (2015/06/16)
Site reactivity of some enol-imines derived from N-aryl formamides with pentachloropyridine under basic conditions in dry CH3CN was investigated. The aromatic nucleophilic substitution of pentachloropyridine with enol-imines occurs at the 4-position of pyridine ring by both oxygen and nitrogen site of enol-imines. Nucleophilic attack by the oxygen of enol-imine gave corresponding oximino compounds as a mixture of E- and Z-isomers. In contrast, nucleophilic attack by the nitrogen of enol-imine gave the unexpected N,N-di-substituted aryl compounds. The structures of all the compounds were confirmed by IR, 1H NMR, 13C NMR and 19F NMR spectroscopy as well as elemental analysis and X-ray crystallography.