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1 2009

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Preparation and Structure of Optically Active Imidazolium Tetrafluoroborates; in Search of New Chiral Ionic Liquids

Mlostoń G., Mucha P., Tarka R., Urbaniak K., Linden A., Heimgartner H.

Polish Journal of Chemistry

2009

Vol. 83, nr 6

1105-1114

Enantiomerically pure (R)-1-(1-phenylethyl)imidazoles 4a,b can be prepared conveniently from alfa-(hydroxyimino)ketones 1, (R)-1-phenylethylamine and form aldehyde, fol lowed by deoxygenation with Raney-Ni. Similarly, the reaction with (R,R)-trans-cyclohexane-1,2-diamine yields enantiomerically pure (R,R)-trans-1,1'-cyclohexane-1,2-diyl)imidazoles 4c,d. Alkylation of these imidazole derivatives with alkylbromides leads to the corresponding 3-alkylimidazolium bromides 6 and 8, respectively, which on treatment with sodium tetrafluoroborate are transformed into the correspond ing tetrafluoroborates 7 and 9. Whereas some of the imidazolium salts 7 show properties of chiral ionic liquids, the bis-imidazolium tetrafluoroborates 9 are high-melting crystalline materials.