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Abstract. In a two step reaction, hexamethylbenzene consumes two molecules of singlet oxygen to form epidioxy hydroperoxide 3. The first step involves a [4 + 2]-cycloaddition, which is followed by an ene-reaction. The structure of the intermediary endoperoxide 2 has been established spectroscopically. Pentamethylbenzene reacts in the same way with singlet oxygen, albeit much more slowly. Two epidioxy hydroperoxides are formed in this case.

The title compounds have been prepared in 70-90% yield by epoxidation of appropriate cyclopropylidene compounds with KHSO, in a phosphate buffer in the presence of acetone. The latter is converted into an unstable dioxirane, which acts as the oxygen-transferring agent.

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