Silver (I) Oxide Catalyzed Oxidation of o-Allyl-and o-(1-Propenyl) phenols.

MR Iyer, GK Trivedi

Index: Iyer, Meera R.; Trivedi, Girish K. Bulletin of the Chemical Society of Japan, 1992 , vol. 65, # 6 p. 1662 - 1664

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Citation Number: 17

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.