Dimethyl(methylthio)sulfonium tetrafluoroborate can be used as an electrophilic sulfenylating agent, capable of reacting with nucleophilic atoms; reacting with electron-rich olefins to promote addition reactions, cyclization reactions; and activating dithioacetals, trithioorthoesters, and thioglycosides to undergo carbon-carbon or carbon-heteroatom bond formation reactions.
DMTSF can be conveniently prepared from Dimethyl Disulfide and Trimethyloxonium Tetrafluoroborate (Me3O+ BF4 -) in MeCN. Precipitation of the product results after addition of ether and isolation requires filtration under anhydrous conditions.
DMTSF must be stored under anhydrous conditions, preferably in a well sealed bottle under nitrogen. Exposure to moisture results in a stench and the reagent is corrosive. Use in a fume hood.
