Abstract
A new Stereospecific epoxidation with α-azohydroperoxides (1) in basic media is reported. cis- and trans-Stilbene gave the corresponding epoxides stereospecifically in the reaction with α-azohydroperoxides (1a–d) catalysed by pyridine or sodium hydroxide. Similarly, cis-β-methylstyrene gave the corresponding cis-epoxide. Cyclohexene, trinorborn-2-ene, and tetramethylethylene all gave epoxides in good to high yield in the reaction with (1a–d) under the basic conditions. The mechanism of this novel base-catalysed epoxidation is discussed.
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