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

Poorfreidoni, A ; Sharif University of Technology | 2015

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  1. Type of Document: Article
  2. DOI: 10.1039/c5nj00418g
  3. Publisher: Royal Society of Chemistry , 2015
  4. Abstract:
  5. 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
  6. Keywords:
  7. Formamide ; Formamide derivative ; Imine ; Methyl group ; Nitrogen ; Nucleophile ; oxygen ; Pentachloropyridine ; Pyridine ; Unclassified drug ; Carbon nuclear magnetic resonance ; Chemical structure ; Fluorine nuclear magnetic resonance ; Nucleophilicity ; Priority journal ; Proton nuclear magnetic resonance ; Reaction time ; Room temperature ; Substitution reaction ; Temperature ; Ultrasound ; X ray crystallography
  8. Source: New Journal of Chemistry ; Volume 39, Issue 6 , 2015 , Pages 4398-4406 ; 11440546 (ISSN)
  9. URL: http://pubs.rsc.org/en/Content/ArticleLanding/2015/NJ/C5NJ00418G