Low melting N-4-functionalized-1-alkyl or polyfluoroalkyl-1,2,4-triazolium salts

Butane sulfobetaines 2a,b, zwitterionic oxo perfluorocarboxylates 3a,b, and functionalized triazolium bromides 4b,c and 5a-c have been synthesized and subsequently reacted to give a series of hydrophilic and hydrophobic fluorinated and nonfluorinated N-1-alkyl-N-4-functionalized-triazolium compounds (6a-11b). With the exception of 11b (mp 41 degreesC), all are liquids at room temperature. Metathesis of the fluorinated quaternary triazolium halides with other anions led to the formation of a new class of compounds, namely, [(R)(R-funct)-Taz]Y-+(-), Y = PF6, (CF3SO2) N-2, and CF3SO3, in good isolated yields. All of the new compounds were characterized by H-1, F-19, and C-13 NMR, and MS spectral and elemental analyses. Thermal analyses indicate that high temperatures are attainable prior to decomposition. DSC studies show glass transitions for several samples, and all functionalized compounds, 5-11, have T(g)s or T(m)s <100 degreesC. Densities range between 1.4 and 1.61 g cm(-3). 1-Heptyl-4-(butyl-4-sulfonic acid) triazolium trifluoromethanesulfonate, 6b, in its role as a Bronsted acid, is an effective solvent/catalyst for high yield esterification and hetero-Michael addition reactions and may be recycled for repetitive use.