Abstract
(Polyfluoroalkyl)trimethylammonium iodides ( 1a–d), R fCF 2CH 2N +Me 3I − (R f −, a = HCF 2, b = CF 3, c = H(CF 2) 3, d = H(CF 2) 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), R fCFCHN +Me 3I −, quantitatively. However, treatment of 1 with 3 equimolaramounts of sodium hydroxide yielded different products depending on the length of the R fchain: 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 betaine 6; 1c and 1d afforded the corresponding 1 H,ω H-perfluoroalkanes 7c and 7d, respectively,together with 6.
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