Reactions of 9,10-dioxatricyclo[6.2.2.01,6]dodeca-3,11-dien-6-yl hydroperoxide: synthesis of oxygenated naphthalene derivatives

We synthesized 9,10-dioxatricyclo[6.2.2.01,6]dodeca-3,11-dien-6-yl hydroperoxide (7) and investigated for the first time its further chemical transformation with dimethylsulfide, NEt3, PPh3, and Co–TPP, respectively. A variety of stereospecifically oxygenated compounds were obtained from these reactions containing different functional groups such as alcohols, ketone, and epoxides.