title: Ethylammonium nitrate (EAN)/Tf2O and EAN/TFAA: ionic liquid based systems for aromatic nitration.
abstract: Acting as in situ sources of triflyl nitrate (TfONO(2)) and trifluoroacetyl nitrate (CF(3)COONO(2)), the EAN/Tf(2)O and EAN/TFAA systems, 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/Tf(2)O is superior to EAN/TFAA for nitration of strongly deactivated systems. Both systems exhibit low substrate selectivity (K(T)/K(B) = 5-10) in between values reported for covalent nitrates and preformed nitronium salts.
authors.affiliation: Department of Chemistry, University of North Florida, 1 UNF Drive, Jacksonville, Florida 32224, United States.
authors.forename: Gopalakrishnan
authors.initials: G
authors.lastname: Aridoss
authors.forename: Kenneth K
authors.initials: KK
authors.lastname: Laali