Autoxidation of 2-alkylidene-1,3-cyclohexanediones as a green process to form bicyclic hemiketal endoperoxides

Abstract

Autoxidation of 2-alkylidene-1,3-cyclohexanediones exclusively furnishes endoperoxides and could constitute an interesting green process to prepare hemiketal endoperoxides useful in medicinal chemistry. Autoxidation of 2-alkylidene-1,3-cycloheptanediones into endoperoxides is very slow while autoxidation of 2-alkylidene-1,3-cyclopentanediones leads to mixtures of oxidized products.