Merging the chemistry of electron-rich olefins with imidazolium ionic liquids: radicals and hydrogen-atom adducts

To probe the reactivity of ionic liquids relevant to their use in electrochemical applications, the ionic liquid 1-ethyl-3-methylimidazolium tetrachloroaluminate(III) was reacted with metallic lithium to produce a persistent radical, which can be considered a hydrogen-atom adduct of an electron-rich olefin (ERO). Reaction of tetrakis(dimethylamino) ethene, a bona fide ERO, with muonium, produces a structurally similar radical.