Epoxyisophorone ring-opening: an efficient route for the introduction of functional groups at position 2 of isophorone

Functional groups were selectively introduced at the C-2 position of isophorone via the epoxide ring-opening with several nucleophiles. Various behaviours were observed depending on the reaction conditions and the nature of nucleophilic reagents. Electronic and steric effects of the reactants were discussed. The best experimental systems involved LiClO4 salt effect in acetonitrile, phase transfer catalysis or KF–alumina under solvent-free conditions under microwaves.