The photo‐oxidation of hexamethylbenzene by singlet oxygen

Abstract

Abstract In the dye‐sensitized photo‐oxidation of hexamethylbenzene two molecules of singlet oxygen are rapidly taken up: one of the oxygenation steps involved is an ene‐type reaction, and the other a [4 + 2]‐cycloaddition. The resulting endoperoxy hydroperoxide 2 can be reduced selectively to the corresponding endoperoxy alcohol 3 and by further reduction to the triol 4 . X‐ray analysis shows the hydroperoxy group and the OO bridge in 2 to be on different sides of the cyclohexyl ring.