Amphiphilic perfluoroalkylated sulfones and sulfonate betaines

Two types of perfluoro alkyl-containing amphiphilic sulfones 7–9 and 13–15, respectively, and sulfonate betaines 23–32 were prepared using 2-[(perfluoroalkyl)methyl]oxiranes (1–3, RF = C4F9, C6F13, C8F17) or 3-(perfluoroalkyl)propyl iodides (16 and 17, RF = C6F13, C8F17) as the starting compounds. The overall yields of two-step syntheses were above 90%. The compounds 7–9 were prepared by the reaction of oxiranes 1–3 with 2-sulfanylethan-l-ol and subsequent oxidation of intermediate sulfides. Similarly, the amphiphiles 13–15 were obtained by analogous reaction of oxiranes 1–3 with thiomorpholine and subsequent oxidation of the sulfur atom in the morpholine ring. In the syntheses of betaines 23–32, the starting compounds 1–3 or 16 and 17 were first reacted with dimethylamine followed by the ring-opening reaction of the intermediate fluoroalkyl(dimethyl)amines with propane-1,3- or butane-1,4-sultones.