Amphiphilic perfluoroalkylated sulfones and sulfonate betaines

Abstract

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, R F = C 4F 9, C 6F 13, C 8F 17) or 3-(perfluoroalkyl)propyl iodides ( 16 and 17, R F = C 6F 13, C 8F 17) 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.