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


Mloston, G; Mucha, P; Tarka, R; Urbaniak, K; Linden, A; Heimgartner, H (2009). Preparation and Structure of Optically Active Imidazolium Tetrafluoroborates; in Search of New Chiral Liquids. Polish Journal of Chemistry, 83(6):1105-1114.

Abstract

Enantiomerically pure (R)-1-(1-phenylethyl)imidazoles 4a,b can be prepared conveniently from alpha-(hydroxyimino)ketones 1, (R)-1-phenylethylamine and formaldehyde, followed 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 corresponding 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.

Abstract

Enantiomerically pure (R)-1-(1-phenylethyl)imidazoles 4a,b can be prepared conveniently from alpha-(hydroxyimino)ketones 1, (R)-1-phenylethylamine and formaldehyde, followed 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 corresponding 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.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:June 2009
Deposited On:25 Nov 2009 07:23
Last Modified:06 Dec 2017 21:43
Publisher:Polskie Towarzystwo Chemiczne
ISSN:0137-5083
Funders:Polish Ministry of Science and Higher Education, F. Hoffmann-La roche AG, Basel
Official URL:http://malina.ichf.edu.pl/pjch/pj-2009.htm

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