Sulfur Dioxide → Sulfur Dioxide

Participants

Reaction Steps

A solution of sulfur dioxide was prepared by bubbling sulfur dioxide (3.9 g, 61 mmol) in a solution of anhydrous acetonitrile (20 ml) at ambient temperature. This solution was added to PhSCF2SiMe3 (4.3 g, 18.4 mmol, obtained according to the procedure from example 6) and stirred at ambient temperature under an inert atmosphere. Anhydrous CsF (2.8 g, 18.5 mmol) was then added to the reaction mixture, which was stirred at ambient temperature overnight. The reaction was monitored by TLC and by 19F NMR (CDCl3) until the disappearance of PhSCF2SiMe3. F-TEDA (7.15 g, 20 mmol) was added to the mixture, at −20° C., which was then stirred for 1 h at ambient temperature. The mixture was concentrated and the solid residue washed with ethyl ether (10×50 ml). The filtrate was evaporated and the product purified by bulb-to-bulb distillation. The product difluoro(phenylsulfanyl)methanesulfonyl fluoride was obtained in the form of a colorless liquid (2.5 g, 57%).

Provenance & Evidence