Silver(I) Oxide Catalyzed Oxidation of <i>o</i>-Allyl- and <i>o</i>-(1-Propenyl)phenols

Abstract

Abstract The oxidation behavior of o-alkenylphenols towards a one-electron transfer agent, silver(I) oxide, was studied. Oxidation of an o-(1-alkenyl)phenol yields a dimeric product via the intermediacy of a quinonemethide radical. However, in the case of an o-(2-alkenyl)phenol where the γ-carbon bears substituents, a 2H-chromene is the product. During the course of this study, carpanone, a naturally-occurring lignan, was synthesized.