ReactNMR and ReactIR as Reaction Monitoring and Mechanistic Elucidation Tools: The NCS Mediated Cascade Reaction of α-Thioamides to α-Thio-β-chloroacrylamides
The Journal of Organic Chemistry2011Vol. 76(23), pp. 9630–9640
Citations Over TimeTop 11% of 2011 papers
David A. Foley, Christopher W. Doecke, Jonas Y. Buser, Jeremy M. Merritt, Linda Murphy, Marie Kissane, Stuart G. Collins, Anita R. Maguire, Andreas Kaerner
Abstract
On-flow ReactIR and (1)H 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.
Related Papers
- → Synthesis and Applications of Chalcogenoamide: Thio-, Seleno- and Telluroamides(2007)47 cited
- → Regioselective (thio)carbamoylation of 2,7-di-tert-butylpyrene at the 1-position with iso(thio)cyanates(2017)5 cited
- → ChemInform Abstract: STUDIES OF THIO AMIDES AND AMIDES‐ CONVERISON OF THIO AMIDES INTO AMIDES BY TRIMETHYLOXONIUM FLUOROBORATE(1977)
- → ChemInform Abstract: SYNTHESIS OF AROMATIC THIO ACID AMIDES FROM BENZYL THIO ETHERS BY THIOLATION(1977)
- → Tentative Assignments of Fundamental Vibrations of Thio- and Selenoamides. X. The Influence of S-Methylation on the Characteristic Thioamide Bands in 1,2-Dimethyl-3-pyrazolidinethione.(1982)