Triethylamine → 10-(Ethenesulfonyl)-1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluorodecane

Participants

Reaction Steps

2-(Perfluorooctyl)ethanyl 2-chloroethanyl sulfone (RF =C8F17, 5.74 g, 10.0 mmole) was dissolved in 40 ml of tetrahydrofuran (THF) at 45°, while stirring in a constant temperature oil bath. Triethylamine (1.52 g, 2.10 ml, 15.0 mmole) in 10 ml of THF was added and an exotherm carried the temperature to 51°. A precipitate of white solid triethylammonium chloride immediately began to form. After 1 hour at 45° the slurry was filtered while hot (Buchner funnel), rinsed with diethyl ether twice, and the clear filtrate evaporated on a rotary evaporator. The dry solid Et3N HCl weighed 1.35 g, 98.8% of theory. The evaporated solid 2-(perfluoro-octyl)ethanyl vinyl sulfone was taken to 40°/15 mm and weighed 5.38 g, 100% of theory; mp sinter 92° melt 93°-94.5°. The sulfone was heated further to 155° without evidence of decomposition. The sulfone was soluble in chloroform, and insoluble in carbon tetrachloride, benzene or ligroine (bp 60°-70°). The sulfone dissolved in hot benzene, but was insoluble in hot ligroine. A 1.00 g sample was dissolved in 8.0 ml of benzene by heating on a steam bath, with care to prevent foaming over; 8.0 ml of ligroine was added and the clear, colorless solution when cool gave 0.77 g of solid, mp sinter 94° melt 95°-96°. When concentrated to 4.0 ml volume a fraction, 0.11 g, mp 96°-97° was obtained. The original sample gave a single spot in TLC analysis. The infrared spectrum was identical to that of the C6 homolog of Example 1. The NMR spectrum was consistent with the proposed structure and resembled closely that obtained from the C6 homolog.

Provenance & Evidence