Abstract
The kinetics of the reactions of ethenesulfonyl fluoride (ESF) with sulfonium and pyridinium ylides were measured photometrically to determine the electrophilicity parameter of ESF according to the correlation lgk(20 degrees C)=s(N)(N+E). With E=-12.09, ESF is among the strongest Michael acceptors in our comprehensive electrophilicity scale, which explains its excellent performance in reactions with many nucleophiles. Its predicted usability as a reagent in electrophilic aromatic substitutions with electron-rich arenes was confirmed by uncatalyzed reactions with alkyl-substituted pyrroles.
| Item Type: | Journal article |
|---|---|
| Faculties: | Chemistry and Pharmacy > Department of Chemistry |
| Subjects: | 500 Science > 540 Chemistry |
| ISSN: | 1433-7851 |
| Language: | English |
| Item ID: | 48451 |
| Date Deposited: | 27. Apr 2018, 08:15 |
| Last Modified: | 04. Nov 2020, 13:26 |
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