Aqueous Micellar Systems Formed by Surfactant Ionic Liquids. Application in Diels-Alder Reactions ^†

In the present work, our objective is to take advantage of the property presented by Ionic Liquids (ILs) based on 1-alkyl-3-methylimidazolium cations by having amphiphilic character when the alkyl group is a long hydrocarbon chain. These ILs can act as surfactants forming micelles in aqueous solution. In this sense, the micellar effect on a Diels-Alder reaction (DA) was analyzed taken as a reference. The reactive system studied consists of maleic anhydride and isoprene, variables such as diene:dienophile ratio and reaction temperatura among the most important were optimized. N,N-dodecylmethylimidazolium bromide was used at the critical micellar concentration (CMC) of 1 × 10⁻² M. These “new systems” microheterogeneous would allow, in addition to better solubilization of non-polar substrates, to adopt milder reaction conditions.