Friday, April 24, 2009

preparation of [Me2SSMe+][BF4-] (DMTSF)

what DMTSF can do?
electrophilic sulfenylation reagent capable of reacting with nucleophilic atoms;2 reacts with electron-rich alkenes to promote addition reactions,3 cyclizations;4 activates dithioacetals,5 trithioorthoesters,6 and thioglycosides7 for carbon–carbon or carbon–heteroatom bond forming reactions). from e-EROS Encyclopedia of Reagents for Organic Synthesis.

Inorganic Chemistry, Vol. 42, No. 8, 2003
Following the published procedure,
solution containing 0.74 mL of methyl disulfide (8.06 mmol) in
7 mL of CH3CN was added dropwise to an equimolar amount of
Me3O+BF4- (1.04 g, 8.06 mmol) dissolved in 8 mL of CH3CN
at 0 °C. After the mixture had been stirred for 2 h at 0 °C, dry
ether was added to precipitate dimethylthiomethylsulfonium fluoroborate
([Me2SSMe+][BF4-]) as a white solid that was stored in
the glovebox at -36 °C (1.1 g; yield, 69%).

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