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Electrophilic tetraalkylammonium nitrate nitration. II. Improved anhydrous aromatic and heteroaromatic mononitration with tetramethylammonium nitrate and triflic anhydride, including selected microwave examples.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2003 Jan 24 , DOI: 10.1021/jo026202q
Scott A. Shackelford 1 , Mark B. Anderson 1 , Lance C. Christie 1 , Thomas Goetzen 1 , Mark C. Guzman 1 , Martha A. Hananel 1 , Wayne D. Kornreich 1 , Haitao Li 1 , Ved P. Pathak 1 , Alex K. Rabinovich 1 , Ranjan J. Rajapakse 1 , Larry K. Truesdale 1 , Stella M. Tsank 1 , Haresh N. Vazir 1
Affiliation  

A new one-pot nitration employing tetramethylammonium nitrate and trifluoromethanesulfonic anhydride in dichloromethane to provide a ready source of the nitronium triflate nitrating agent is presented. Rapid and selective nitration with a variety of aromatic and heteroaromatic substrates is achieved resulting in the synthesis of several novel organic compounds. A distinct advantage is the removal of undesired byproducts by aqueous workup. This very mild nitration permits large-scale syntheses and gives high isolated product yields that often require no further purification. This tetramethylammonium nitrate-based nitration also has been applied to microwave-assisted conditions, and the results with several compounds are outlined.

中文翻译:

亲电四烷基硝酸铵硝化。二。用硝酸四甲基铵和三氟甲磺酸酐改进无水芳族和杂芳族单硝化反应,包括选定的微波实例。

提出了一种新的一锅式硝化方法,该方法采用硝酸四甲基铵和三氟甲磺酸酐在二氯甲烷中的溶液,以提供易于使用的三氟甲磺酸硝化硝化剂的来源。实现了多种芳香族和杂芳香族底物的快速选择性硝化,从而合成了几种新型有机化合物。一个明显的优点是通过水后处理除去不需要的副产物。这种非常温和的硝化作用可实现大规模合成,并获得较高的分离产物收率,而通常无需进一步纯化。这种基于硝酸四甲基铵的硝化也已应用于微波辅助条件,并概述了几种化合物的结果。
更新日期:2017-01-31
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