A new epoxidation reaction: base-catalysed stereospecific epoxidation with α-azohydroperoxides

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.