Electron rich ionic liquids: New chemistry and applications

I&EC 223

Jason Clyburne, clyburne@sfu.ca, Taramatee Ramnial, tramnial@sfu.ca, Michelle Hauser, and Wood Bryan. Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, BC V5A 1S6, Canada
Perhaps one of the most significant and detrimental side reactions of many ionic liquids is their reactivity with basic or electron rich species. In many cases deprotonation reactions or decomposition of the ionic liquid through electrochemical processes results in unwanted side reactions. This report will document several of the important reactions of imidazolium ions (and other common cations) with electron rich species, and will show that these problems can, in many cases, be circumnavigated using phosphonium ionic liquids. We have prepared new solutions of the phosphonium ionic liquids containing reactive species such as borane and Grignard reagents, and have studied their reactivity in some details. For instance, Grignard reagents form persistent solutions in phosphonium ionic liquids, and in this highly polar media, they undergo facile electron transfer reactions that are unprecedented in molecular solvents. Extensive reactivity studies will be reported, featuring identification of diamagnetic and radical intermediates, and structural studies will also be used to illustrate the important inter-ion interactions involving complex anions.