Abstract
Abstract (Polyfluoroalkyl)trimethylammonium iodides (1a–d), RfCF2CH2N+Me3I− (Rf−, a = HCF2,b = CF3, c = H(CF2)3, d = H(CF2)5), reacted easily with an equimolar amount of sodiumhydroxide in water at 20°C to give Z isomers of (polyfluoro-1-alkenyl)trimethylammoniumiodides (2a–d), RfCFCHN+Me3I−, quantitatively. However, treatment of 1 with 3 equimolaramounts of sodium hydroxide yielded different products depending on the length of the Rfchain: la gave (2-oxo-3,3-difluoropropyl)trimethylammonium iodide (3a), which had a greattendency to form the hydrate 4a; 1b produced a mixture of the analogous ketone 3b and betaine6; 1c and 1d afforded the corresponding 1H,ωH-perfluoroalkanes 7c and 7d, respectively,together with 6.
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