Peroxide oxidation of Δ4-3-ketosteroids

HL Holland, E Riemland…

Index: Holland, Herbert L.; Riemland, Elly; Ulrich, Daum Canadian Journal of Chemistry, 1982 , vol. 60, p. 1919 - 1923

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Citation Number: 14

Abstract

Treatment of Δ4-3-ketosteroids with tert-buly hydroperoxide in the presence of lithium hydroxide leads to the formation of the corresponding 4β, 5β epoxides stereospecifically and in good yield. The stereospecificity of this reaction is explicable in terms of the accepted mechanism for the hydrogen peroxide epoxidation of Δ4-3-ketosteroids. The use of aqueous sodium peroxide as oxidant leads to the production of the corresponding Δ4-3, 6-diones. ...