Department of Chemistry, University of North Florida, 1 UNF Drive, Jacksonville, Florida 32224, United States.
J Org Chem. 2011 Oct 7;76(19):8088-94. doi: 10.1021/jo201374a. Epub 2011 Sep 13.
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.
作为三氟甲磺酸硝酸盐（TfONO(2)）和三氟乙酰硝酸盐（CF(3)COONO(2)）的原位源，通过在易得的乙基硝酸铵（EAN）离子液体溶剂中进行复分解反应生成的 EAN/Tf(2)O 和 EAN/TFAA 体系是用于广泛的芳香族和杂芳香族化合物的强亲电硝化试剂。比较硝化实验表明，EAN/Tf(2)O 比 EAN/TFAA 更适合于强失活体系的硝化。这两个体系在报道的共价硝酸酯和预形成的硝鎓盐之间表现出低的底物选择性（K(T)/K(B)=5-10）。
