ReactNMR and ReactIR as Reaction Monitoring and Mechanistic Elucidation Tools: The NCS Mediated Cascade Reaction of 伪-Thioamides to 伪-Thio-尾-chloroacrylamides

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• 作者：David A. Foley ; Christopher W. Doecke ; Jonas Y. Buser ; Jeremy M. Merritt ; Linda Murphy ; Marie Kissane ; Stuart G. Collins ; Anita R. Maguire ; Andreas Kaerner
• 刊名：Journal of Organic Chemistry
• 出版年：2011
• 出版时间：December 2, 2011
• 年：2011
• 卷：76
• 期：23
• 页码：9630-9640
• 全文大小：705K
• 年卷期：v.76,no.23(December 2, 2011)
• ISSN：1520-6904

文摘

On-flow ReactIR and ¹H NMR reaction monitoring, coupled with in situ intermediate characterization, was used to aid in the mechanistic elucidation of the N-chlorosuccinimide mediated transformation of an 伪-thioamide. Multiple intermediates in this reaction cascade are identified and characterized, and in particular, spectroscopic evidence for the intermediacy of the chlorosulfonium ion in the chlorination of 伪-thioamides is provided. Further to this, solvent effects on the outcome of the transformation are discussed. This work also demonstrates the utility of using a combination of ReactIR and flow NMR reaction monitoring (ReactNMR) for characterizing complex multicomponent reaction mixtures.