IRIS publication 160748395
ReactNMR and ReactIR as Reaction Monitoring and Mechanistic Elucidation Tools: The NCS Mediated Cascade Reaction of alpha-Thioamides to alpha-Thio-beta-chloroacrylamides
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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 -
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@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} }
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AUTHORS | Foley, DA,Doecke, CW,Buser, JY,Merritt, JM,Murphy, L,Kissane, M,Collins, SG,Maguire, AR,Kaerner, A | ||
YEAR | 2011 | ||
MONTH | January | ||
JOURNAL_CODE | The Journal of Organic Chemistry | ||
TITLE | ReactNMR and ReactIR as Reaction Monitoring and Mechanistic Elucidation Tools: The NCS Mediated Cascade Reaction of alpha-Thioamides to alpha-Thio-beta-chloroacrylamides | ||
STATUS | Validated | ||
TIMES_CITED | () | ||
SEARCH_KEYWORD | RESOLUTION NMR-SPECTROSCOPY FLOW NMR ONLINE NMR CHEMICAL-REACTIONS IN-SITU INTERMEDIATE 2,4,6-TRINITROANISOLE TRANSFORMATION KINETICS STEP | ||
VOLUME | 76 | ||
ISSUE | |||
START_PAGE | 9630 | ||
END_PAGE | 9640 | ||
ABSTRACT | 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. | ||
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DOI_LINK | DOI 10.1021/jo201212p | ||
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