Ionic Liquid As Catalyst and Reaction Medium. The Dramatic Influence of a Task-specific Ionic Liquid, [bmIm]OH, in Michael Addition of Active Methylene Compounds to Conjugated Ketones, Carboxylic Esters, and Nitriles

[reaction: see text] A task-specific ionic liquid, [bmIm]OH, has been introduced as a catalyst and as a reaction medium in Michael addition. Very interestingly, although the addition to alpha,beta-unsaturated ketones proceeds in the usual way, giving the monoaddition products, this ionic liquid always drives the reaction of open-chain 1,3-dicarbonyl compounds with alpha,beta-unsaturated esters and nitriles toward bis-addition to produce exclusively bis-adducts in one stroke.