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

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Title: ReactNMR and ReactIR as Reaction Monitoring and Mechanistic Elucidation Tools: The NCS Mediated Cascade Reaction of α-Thioamides to α-Thio-β-chloroacrylamides
Authors: David A. Foley, Christopher W. Doecke, Jonas Y. Buser, Jeremy M. Merritt, Linda Murphy, Marie Kissane, Stuart G. Collins, Anita R. Maguire, and Andreas Kaerner
Date: 2011/10/26
Reference: J. Org. Chem., 2011, 76 (23), pp 9630–9640
DOI: http://dx.doi.org/10.1021/jo201212p
Download link:  http://pubs.acs.org/doi/abs/10.1021/jo201212p

 

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 α-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 α-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.

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