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

✍ Scribed by Dongbin Zhao; Zhaofu Fei; Tilmann J. Geldbach; Rosario Scopelliti; Gábor Laurenczy; Paul J. Dyson

• Publisher: John Wiley and Sons
• Year: 2005
• Tongue: German
• Weight: 203 KB
• Volume: 88
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200590046

✦ Synopsis

Abstract

The two known Me‐ and allyl‐substituted 1__H__‐imidazol‐3‐ium bromides 1 and 2, respectively, were converted to the corresponding BF$\rm{_{4}^{-}}$ and BPh$\rm{_{4}^{-}}$ salts 3–6 (Scheme 1). Compounds 3 and 4 were liquids at ambient temperature. Reaction of 1 or 2 with [PdCl~2~] 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 H~2~ pressure). The solid‐state structures of compounds 5–7 and 9 were solved by means of single‐crystal X‐ray analyses (Figs. 1–4).