Microwave-assisted and light-induced catalytic ring opening of α-epoxyketones using DDQ

Ring opening reaction of α-epoxyketones in the presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in methanol solution under microwave and UV irradiations resulted in the formation of α-hydroxy-β-methoxyketones through Cβ–O bond cleavage in excellent yields. Whereas the nature and location of the additional substituent affect the rate of ring opening, microwave irradiation remarkably raised the rate of reactions compared with UV-light. Cyclic voltammetric and conductometric studies supported these experimental results.

Graphical abstractRing opening reaction of α-epoxyketones in the presence of DDQ in methanol solution under microwave and UV irradiations results in the formation of α-hydroxy-β-methoxyketones through Cβ–O bond cleavage in excellent yields. Whereas the nature and location of the additional substituent affect the rate of ring opening, microwave irradiation remarkably raises the rate of reactions compared with UV-light. Cyclic voltammetric and conductometric studies support these experimental results. Figure optionsDownload full-size imageDownload as PowerPoint slide