1-FLUORO-4-HYDROXY-1,4-DIAZONIABICYCLO [2.2.2]OCTANE BIS(TETRAFLUOROBORATE) AS A NEW, EFFECTIVE REAGENT FOR SELECTIVE FLUOROFUNCTIONALISATION OF ALKENES UNDER MILD REACTION CONDITIONS

-Fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluorobora te) (Accufluor(TM) NFTh) is confirmed as a highly effective reagent fo r introducing a fluorine atom into organic molecules across a phenyl-s ubstituted carbon-carbon double bond. Quantitative and Markovnikov-typ e regioselective formation of vicinal fluoro-hydroxy, fluoro-methoxy o r fluoro-acetoxy adducts was achieved when phenyl-substituted alkenes were treated with a MeCN solution of NFTh in the presence of water, me thanol or acetic acid. The stereochemical course of fluoro-methoxylati on reactions in the case of cyclic phenyl-substituted alkenes depends strongly on the structure of the alkene.