WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow, G1 1XL (UK).
Angew Chem Int Ed Engl. 2013 Oct 25;52(44):11470-87. doi: 10.1002/anie.201301837. Epub 2013 Oct 16.
Most synthetic chemists will have at some point utilized a sterically demanding secondary amide (R2 N(-) ). The three most important examples, lithium 1,1,1,3,3,3-hexamethyldisilazide (LiHMDS), lithium diisopropylamide (LiDA), and lithium 2,2,6,6-tetramethylpiperidide (LiTMP)-the "utility amides"-have long been indispensible particularly for lithiation (Li-H exchange) reactions. Like organolithium compounds, they exhibit aggregation phenomena and strong Lewis acidity, and thus appear in distinct forms depending on the solvents employed. The structural chemistry of these compounds as well as their sodium and potassium congeners are described in the absence or in the presence of the most synthetically significant donor solvents tetrahydrofuran (THF) and N,N,N',N'-tetramethylethylenediamine (TMEDA) or closely related solvents. Examples of hetero-alkali-metal amides, an increasingly important composition because of the recent escalation of interest in mixed-metal synergic effects, are also included.
大多数合成化学家在某些时候都会使用空间位阻要求较高的仲酰胺（R2N(-)）。其中最重要的三个例子是，六甲基二硅叠氮化锂（LiHMDS）、二异丙基胺化锂（LiDA）和 2,2,6,6-四甲基哌啶锂（LiTMP）——“通用酰胺”，它们长期以来对于锂化（Li-H 交换）反应特别不可或缺。与有机锂化合物一样，它们表现出聚集现象和强路易斯酸性，因此根据所使用的溶剂呈现出不同的形式。这些化合物以及它们的钠和钾同系物的结构化学，无论是在最有合成意义的给电子溶剂四氢呋喃（THF）和 N,N,N',N'-四甲基乙二胺（TMEDA）或密切相关的溶剂存在下，还是在它们不存在的情况下，都有描述。由于最近对混合金属协同效应的兴趣增加，杂碱金属酰胺的例子也被包括在内，它们是越来越重要的组成部分。
