Survey reactivity of some N-aryl formamides with pentafluoropyridine

Add time:08/10/2019    Source:sciencedirect.com

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.

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