Prweparation and thermal stability of optically active 1, 2, 4-triazolium-based ionic liquids

Abstract

The synthesis of optically active ionic liquids, in a four-step reaction sequence, is described. In the first step an oxirane ring of cyclohexene oxide was opened with 1, 2, 4-triazole, yielding a racemic mixture of (1R,2R)- and (1S,2S)-2-(1H-1, 2, 4-triazol-1-yl)cyclohexanol. Kinetic resolution of the racemate by a lipase catalyzed transesterification with vinyl acetate followed by alkylation (quaternization) of the triazole ring resulted in the appropriate optically active salts formation. After the anion metathesis, thermally stable novel chiral ionic liquids were obtained. © ARKAT-USA, Inc.