Applications of high-potential quinones. Part IV. The mechanism of oxidation of 6-hydroxytetralins

Abstract

Benzylic oxidation of 6-hydroxytetralins by 2,3-dichloro-5,6-dicyanobenzoquinone occurs readily in alcoholic solvents at room temperature. The corresponding 6-hydroxytetralin-1-ones are obtained by the used of two equivalents of the quinone, whereas with one equivalent the major products are 1-alkoxy-derivatives. Isolation of the latter adducts provides evidence for the participation of quinone methides as intermediates in the oxidation process. The role of π-complexes in the initial hydrogen-transfer step is discussed.