71861-99-9Relevant academic research and scientific papers
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.
Survey reactivity of some N-aryl formamides with pentafluoropyridine
Ranjbar-Karimi, Reza,Poorfreidoni, Alireza,Masoodi, Hamid Reza
, p. 222 - 226 (2015/11/03)
Chemo selectivity of some N-aryl formamides with pentafluoropyridine under basic conditions in dry THF was investigated. The aromatic nucleophilic substitution of pentafluoropyridine with enol-imines derived from N-aryl formamides occurs at the 4-position of pyridine ring by both oxygen and nitrogen site of enol-imines depending on the nature of the aromatic ring substituent; with electron releasing group, nucleophilic attack was accomplished by oxygen atom and with an electron withdrawing group, the reaction of N-aryl formamide anions with pentafluoropyridine proceeded via nitrogen site.
