New mechanistic aspects of anodic monofluorination of halogenoalkyl and alkyl phenyl sulphides
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 15,p. 1027-1029
- https://doi.org/10.1039/c39910001027
Abstract
A unique Pummerer type mechanism via fluorosulphonium ions for anodic monofluorination of sulphides is established by comparing the anodic monofluorination of partially halogenated ethyl phenyl sulphides (1, PhSCH2R; R = CF3, CF2H, CFH2, CF2Cl, CClH2) with their anodic methoxylation; simple alkyl phenyl sulphides 2 bearing no electron-withdrawing group could be monofluorinated anodically in satisfactory yields for the first time when tetrahydrofuran was used as a solvent.Keywords
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