Allyl-Functionalised Ionic Liquids: Synthesis, Characterisation, and Reactivity

Authors

  • Dongbin Zhao,

    1. Ecole Polytechnique Fédérale de Lausanne (EPFL), Institut des Sciences et Ingénierie Chimiques, CH-1015 Lausanne, Switzerland (phone: +41-(0)21-693 98 54; fax: +41-(0)21-693 98 85)
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  • Zhaofu Fei,

    1. Ecole Polytechnique Fédérale de Lausanne (EPFL), Institut des Sciences et Ingénierie Chimiques, CH-1015 Lausanne, Switzerland (phone: +41-(0)21-693 98 54; fax: +41-(0)21-693 98 85)
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  • Tilmann J. Geldbach,

    1. Ecole Polytechnique Fédérale de Lausanne (EPFL), Institut des Sciences et Ingénierie Chimiques, CH-1015 Lausanne, Switzerland (phone: +41-(0)21-693 98 54; fax: +41-(0)21-693 98 85)
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  • Rosario Scopelliti,

    1. Ecole Polytechnique Fédérale de Lausanne (EPFL), Institut des Sciences et Ingénierie Chimiques, CH-1015 Lausanne, Switzerland (phone: +41-(0)21-693 98 54; fax: +41-(0)21-693 98 85)
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  • Gábor Laurenczy,

    1. Ecole Polytechnique Fédérale de Lausanne (EPFL), Institut des Sciences et Ingénierie Chimiques, CH-1015 Lausanne, Switzerland (phone: +41-(0)21-693 98 54; fax: +41-(0)21-693 98 85)
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  • Paul J. Dyson

    1. Ecole Polytechnique Fédérale de Lausanne (EPFL), Institut des Sciences et Ingénierie Chimiques, CH-1015 Lausanne, Switzerland (phone: +41-(0)21-693 98 54; fax: +41-(0)21-693 98 85)
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Abstract

The two known Me- and allyl-substituted 1H-imidazol-3-ium bromides 1 and 2, respectively, were converted to the corresponding BFequation image and BPhequation image salts 36 (Scheme 1). Compounds 3 and 4 were liquids at ambient temperature. Reaction of 1 or 2 with [PdCl2] afforded the corresponding 2 : 1 imidazolium/metal complexes 7 and 8. The latter complex, melting at 58°, can be regarded as a ‘true’ ionic liquid. Attempts to polymerise 7 by radical promotion (AIBN) were unsuccessful, but resulted in the centrosymmetric 2 : 1 complex 9. The allyl group of 1 could be arylated (giving rise to 10) or hydrogenated (at 100 bar H2 pressure). The solid-state structures of compounds 57 and 9 were solved by means of single-crystal X-ray analyses (Figs. 1–4).

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