The Reactions of Cholesteryl Acetate with Various Hydroperoxides in the Presence of Tris (acetylacetonato) iron (III) and Hexacarbonylmolybdenum
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概要
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Epoxidation and allylic oxidation of cholesteryl acetate were studied using hydroperoxide (ROOH : R=H, ethyl, iso-propyl, tert-butyl, or cumyl) and a metal complex [Fe (acac)_3 or Mo (CO)_8] in benzene or acetonitrile. In the presence of the iron catalyst, formation of the epimeric C (5,6)-epoxides predominated in the reactions with H_2O_2,while allylic oxidation giving C (7)-ketone, epimeric C (7)-alcohols and C (7)-alkyl peroxides was favored in the reactions with alkyl hydroperoxide, regardless of the polarity of the solvent. The stereoselective β-epoxidation was independent of the structure of ROOH, but the ratio of allylic oxidation to epoxidation was dependent on it. When the iron catalyst was replaced by the molybdenum catalyst, β-epoxidation decreased and solvent effects on the reaction were sufficiently marked to exclude allylic oxidation in the non-polar medium.
- 公益社団法人日本薬学会の論文
- 1980-06-25
著者
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武藤 俊樹
Faculty of Pharmaceutical Sciences, Hokkaido University
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武藤 俊樹
Faculty Of Pharmaceutical Sciences Hokkaido University
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木村 道也
Faculty Of Pharmaceutical Sciences Hokkaido University
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