Abstract
Irradiationof1,4-benzoquinone(BQ)inthepresenceofaseriesofbenzylicethersresultsinan adduct composed of one molecule of quinone and one molecule of the ether. In addition to the formation of this adduct, cleavage of the benzylic ether to the corresponding alde hyde and alcohol was observed. The amount of adduct formed was dramatically increased when the reaction was conducted in benzene. This is in contrast to the results of irradiation with 2,3-dichloro-5,6-dicyanoquinone (DDQ) where no adductwas isolableandonlybondcleavagewas observed. Themajorproductof2,5-dichloroquinone (DCQ) irradiation was bond cleavage of the benzylic ethers, but a small amount of adduct was observed as a reaction product. The formation of adducts in these quinone irradiations can be explained by the slower rate of adduct hydrolysis by lower potential quiñones.