N,N'-Di(alkyloxy)imidazolium Salts: New Patent-free Ionic Liquids and NHC Precatalysts-Reference-Cited by-同舟云学术

N,N'-Di(alkyloxy)imidazolium Salts: New Patent-free Ionic Liquids and NHC Precatalysts

Published:2007-03-01 Issue:3 Volume:62 Page:295-308
ISSN:1865-7117
Container-title:Zeitschrift für Naturforschung B
language:en
Short-container-title:

Author:

Laus Gerhard¹,Schwärzler Alexander²,Schuster Philipp¹,Bentivoglio Gino¹,Hummel Michael¹,Wurst Klaus¹,Kahlenberg Volker³,Lörting Thomas¹,Schütz Johannes⁴,Peringer Paul¹,Bonn Günther⁵,Nauer Gerhard⁶,Schottenberger Herwig¹

Affiliation:

1. Institute of General, Inorganic and Theoretical Chemistry, University of Innsbruck, 6020 Innsbruck, Austria

2. Institute of General, Inorganic and Theoretical Chemistry, University of Innsbruck, 6020 Innsbruck, Austria / Institute of Analytical Chemistry and Radiochemistry, University of Innsbruck, 6020 Innsbruck, Austria

3. Institute of Mineralogy and Petrography, University of Innsbruck, 6020 Innsbruck, Austria

4. Institute of Pharmacy, University of Innsbruck, 6020 Innsbruck, Austria

5. Institute of Analytical Chemistry and Radiochemistry, University of Innsbruck, 6020 Innsbruck, Austria

6. ECHEM Competence Center of Applied Electrochemistry, Viktor-Kaplan-Straße 2, 2270 Wiener Neustadt, Austria

Abstract

1-Hydroxyimidazole-3-oxides (2-H, 2-Me) were alkylated with (RO)2SO2 (R =Me, Et) to give the new 1,3-di(alkyloxy)imidazolium cations which were isolated as hexafluorophosphates. Ion metathesis yielded new hydrophobic ionic liquids (bis(trifluoromethanesulfonyl)imides, tris(pentafluoroethyl) trifluorophosphates). Bromination afforded 2-bromo derivatives which were converted to Ni and Pd N-heterocyclic carbene complexes by oxidative insertion. Fifteen crystal structures were determined by X-ray diffraction. The N-alkyloxy groups are twisted out of the imidazole ring plane and adopt either syn or anti conformations in the solid state.

Publisher

Walter de Gruyter GmbH

Subject

General Chemistry

Link

https://www.degruyter.com/document/doi/10.1515/znb-2007-0301/pdf

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