Synthetically important alkali-metal-utility amides : lithium, sodium and potassium hexamethyldisilazides, diisopropylamides and tetramethylpiperidides
Mulvey, Robert E. and Robertson, Stuart D. (2013) Synthetically important alkali-metal-utility amides : lithium, sodium and potassium hexamethyldisilazides, diisopropylamides and tetramethylpiperidides. Angewandte Chemie International Edition, 52 (44). 11470–11487. ISSN 1433-7851 (https://doi.org/10.1002/anie.201301837)
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Most synthetic chemists will have at some point utilized a sterically demanding secondary amide (R2N−). 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.
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Item type: Article ID code: 47095 Dates: DateEvent25 October 2013PublishedSubjects: Science > Chemistry Department: Faculty of Science > Pure and Applied Chemistry Depositing user: Pure Administrator Date deposited: 04 Mar 2014 11:27 Last modified: 28 Jul 2024 00:57 Related URLs: URI: https://strathprints.strath.ac.uk/id/eprint/47095