Pentafluoroallyl fluorosulphate → 3-Cyanotetrafluoropropionyl fluoride

Participants

Reaction Steps

A solution of 53.9 g (0.2 mole) of methyltriethylammonium-3-cyanotetrafluoropropionate prepared as in Part A in 300 ml of diglyme was stirred at -10° to -5° while 46.0 g (0.20 mole) of perfluoroallyl fluorosulfate was rapidly added. The mixture was then stirred at -10° to -5° for 1 hr., and then at -5° to 0° for 4 hr. Removal of volatiles at 35° (5 mm, 6.7×10-1 kPa) through a liquid N2 trap and fractionation gave 10.0 g (29%) of 3-cyanotetrafluoropropionyl fluoride, bp 19°-20°. IR (gas phase):2265 (CN), 1888 (COF), and 1300-1100 cm-1 (CF) with traces of CO2, SO2F2 and SiF4 present. NMR (CCl4 ; 0°); 19F 25.8 (t of t, JFF 10.1, 5.0 Hz, 1F, COF), -106.7 (d of t, JFF 5.0, 4.6 Hz, 2F, CF2CN), and -118.5 ppm (d of t, JFF 10.1, 4.6 Hz, 2F, CF2C=O).

Provenance & Evidence