Ethylammonium Nitrate (EAN)/Tf2O and EAN/TFAA: Ionic Liquid Based Systems for Aromatic Nitration
Ethylammonium Nitrate (EAN)/Tf2O and EAN/TFAA: Ionic Liquid Based Systems for Aromatic Nitration
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DOI：
10.1021/jo201374a
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发表时间：
2011-10-07
影响因子：
3.6
通讯作者：
Laali, Kenneth K.
中科院分区：
文献类型：
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作者：
Aridoss, Gopalakrishnan;Laali, Kenneth K.
作为硝酸三氟酯(TfONO2)和三氟乙酰硝酸盐(CF3COONO2)的原位来源，EAN/Tf2O和EAN/TFAA体系是在现成的乙基硝酸铵(EAN)离子液体中分解生成的，是多种芳香族和杂芳族化合物的亲电硝化试剂。对比硝化实验表明，EAN/Tf2O对强失活体系的硝化效果优于EAN/TFAA。这两个体系都表现出较低的底物选择性(K-T/K-B=5-10)，介于共价硝酸盐和预制硝酸盐的报告值之间。
Acting as in situ sources of triflyl nitrate (TfONO2) and trifluoroacetyl nitrate (CF3COONO2), the EAN/Tf2O 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/Tf2O 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.