Stereoselectivity of the Diels-Alder reaction in ionic liquids with cyano moieties: effect of the charge delocalization of anions on the relation of solvent-solvent and solute-solvent interactions

In imidazolium ILs, the negative charge delocalization induced by multiple electron-withdrawing cyano groups can be useful in regulating the microscopic environment in imidazolium ILs. For this anion design, the ion-counterion (solvent-solvent) interaction is weakened, the ion-solute (solvent-solute) interaction is facilitated, and the bulkiness of the anion is increased. The electrostatic interaction with the cation has a strong effect on the ion states of the ILs and the stereoselectivity in the Diels-Alder reaction. These regulation methods potentially have wide applications to various useful reactions using ILs.