Jump to main content
Jump to site search

Issue 6, 2015
Previous Article Next Article

Regiochemistry of nucleophilic substitution of pentachloropyridine with N and O bidentate nucleophiles

Author affiliations

Abstract

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.

Graphical abstract: Regiochemistry of nucleophilic substitution of pentachloropyridine with N and O bidentate nucleophiles

Back to tab navigation

Supplementary files

Article information


Submitted
18 Feb 2015
Accepted
18 Mar 2015
First published
18 Mar 2015

New J. Chem., 2015,39, 4398-4406
Article type
Paper
Author version available

Regiochemistry of nucleophilic substitution of pentachloropyridine with N and O bidentate nucleophiles

A. Poorfreidoni, R. Ranjbar-Karimi and R. Kia, New J. Chem., 2015, 39, 4398
DOI: 10.1039/C5NJ00418G

Social activity

Search articles by author

Spotlight

Advertisements