Amphiphilic perfluoroalkylated sulfones and sulfonate betaines |
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Authors: | Robert Kaplánek |
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Institution: | Department of Organic Chemistry, Institute of Chemical Technology, Prague, Technická 5, 16628 Prague 6, Czech Republic |
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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, 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. |
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Keywords: | Perfluoroalkylated amphiphiles Sulfones Sulfonate betaines Epoxide ring-opening Sulfide oxidation |
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