TY  - JOUR
  - Foley, DA,Doecke, CW,Buser, JY,Merritt, JM,Murphy, L,Kissane, M,Collins, SG,Maguire, AR,Kaerner, A
  - 2011
  - January
  - The Journal of Organic Chemistry
  - ReactNMR and ReactIR as Reaction Monitoring and Mechanistic Elucidation Tools: The NCS Mediated Cascade Reaction of alpha-Thioamides to alpha-Thio-beta-chloroacrylamides
  - Validated
  - ()
  - RESOLUTION NMR-SPECTROSCOPY FLOW NMR ONLINE NMR CHEMICAL-REACTIONS IN-SITU INTERMEDIATE 2,4,6-TRINITROANISOLE TRANSFORMATION KINETICS STEP
  - 76
  - 9630
  - 9640
  - On-flow ReactIR and H-1 NMR reaction monitoring, coupled with in situ intermediate characterization, was used to aid in the mechanistic elucidation of the N-chlorosuccinirnide mediated transformation of an alpha-athioarnide. 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 alpha-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.
  - DOI 10.1021/jo201212p
DA  - 2011/01
ER  - 

@article{V160748395,
   = {Foley,  DA and Doecke,  CW and Buser,  JY and Merritt,  JM and Murphy,  L and Kissane,  M and Collins,  SG and Maguire,  AR and Kaerner,  A },
   = {2011},
   = {January},
   = {The Journal of Organic Chemistry},
   = {ReactNMR and ReactIR as Reaction Monitoring and Mechanistic Elucidation Tools: The NCS Mediated Cascade Reaction of alpha-Thioamides to alpha-Thio-beta-chloroacrylamides},
   = {Validated},
   = {()},
   = {RESOLUTION NMR-SPECTROSCOPY FLOW NMR ONLINE NMR CHEMICAL-REACTIONS IN-SITU INTERMEDIATE 2,4,6-TRINITROANISOLE TRANSFORMATION KINETICS STEP},
   = {76},
  pages = {9630--9640},
   = {{On-flow ReactIR and H-1 NMR reaction monitoring, coupled with in situ intermediate characterization, was used to aid in the mechanistic elucidation of the N-chlorosuccinirnide mediated transformation of an alpha-athioarnide. 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 alpha-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.}},
   = {DOI 10.1021/jo201212p},
  source = {IRIS}
}