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

被引：80

作者：

Aridoss, Gopalakrishnan ^{[1
]}

Laali, Kenneth K. ^{[1
]}

机构：

[1] Univ N Florida, Dept Chem, Jacksonville, FL 32224 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 19期

关键词：

SOLVENT-FREE CONDITIONS; NITRIC-ACID; ORGANIC-COMPOUNDS; SILICA-GEL; ANHYDRIDE; CATALYST; REAGENT; MEDIA; SALTS; MILD;

D O I：

10.1021/jo201374a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：8088 / 8094

页数：7

共 9 条

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