36871-92-8Relevant academic research and scientific papers
THE REACTIONS OF CHOLESTERYL ACETATE WITH VARIOUS HYDROPEROXIDES IN THE PRESENCE OF TRIS(ACETYLACETONATO)IRON (III) AND HEXACARBONYLMOLYBDENUM
Kimura, Michiya,Muto, Toshiki
, p. 1836 - 1841 (2007/10/02)
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 in benzene or acetonitrile.In the presence of the iron catalyst, formation of the epimeric C(5,6)-epoxides predominated in the reactions with H2O2, 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 mareked to exclude allylic oxidation in the non-polar medium. - Keywords - alkyl-hydroperoxide; allylic oxidation; cholesterol; epoxide; ferric acetylacetonate; hydrogen peroxide; molybdenum hexacarbonyl; solvent effects; stereoselective epoxidation
