Ethylammonium Nitrate (EAN)/Tf₂O and EAN/TFAA: Ionic Liquid Based Systems for Aromatic Nitration

Gopalakrishnan Aridoss and Kenneth K. Laali*

*Department of Chemistry, University of North Florida, 1 UNF Drive, Jacksonville, Florida 32224, United States, Email: kenneth.laaliunf.edu

G. Aridoss, K. K. Laali, J. Org. Chem., 2011, 76, 8088-8094.

DOI: 10.1021/jo201374a

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Abstract

Triflyl nitrate (TfONO₂) and trifluoroacetyl nitrate (CF₃CO₂NO₂), generated via metathesis in the readily available ethylammonium nitrate (EAN) ionic liquid as solvent, are powerful electrophilic nitrating reagents for a wide variety of aromatic and heteroaromatic compounds. Comparative nitration experiments indicate that EAN/Tf₂O is superior to EAN/TFAA for nitration of strongly deactivated systems.

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Key Words

nitro compounds, ionic liquids

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ID: J42-Y2011-3010