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Communication | Regular issue | Vol 22, No. 4, 1984, pp.725-728
Published online, 1st January, 1970
DOI: 10.3987/R-1984-04-0725
A Base-catalyzed Stereospecific Epoxidation with α-Azohydroperoxides

Takahiro Tezuka* and Masaaki Iwaki

*Department of Chemistry, University of Tsukuba, 1-1-1 Ten-nodai, Tsukuba-shi, Ibaraki, 305-8571, Japan

Abstract

A new stereospecific epoxidation with the α-azohydroperoxide (1) is reported. α-Azohydroperoxides (1a - 1d) epoxidized cis- and trans-stilbenes stereospecifically in the reaction catalyzed by pyridine or sodium hydroxide. Similarly, cyclohexene, norbornylene, and cis-β-methylstyrene all were epoxidized by 1a - 1d in good to high yields in basic media. Reactive species of the epoxidation are discussed.