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 (free Supporting Information)
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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