Oxidation of steroidal 5-en-3 beta-ols with Jones reagent in ether.
The two-phase oxidation of steroidal 5-en-3 beta-ol (via 5-en-3-ones) into corresponding 4-en-3,6-diones in diethyl ether with Jones reagent was investigated. It was found that the system Jones reagent/diethyl ether enables short reaction times and easy isolation of the obtained products. The exclusive abstraction of 4 alpha-hydrogen during oxidation, together with molecular mechanics (MM2), and semiempirical (PM3) calculations, suggest that boat conformation of ring A precedes the formation of corresponding radicals (or cations).
Solaja
B A
BA
Faculty of Chemistry, University of Belgrade, Serbia.
Milić
D R
DR
Dosen-Mićović
L I
LI
D002784:Cholesterol / Q000737:chemistry; D002840:Chromates; D003687:Dehydroepiandrosterone / Q000737:chemistry; D003903:Deuterium / Q000737:chemistry; D004144:Diosgenin / Q000737:chemistry; D004986:Ether; D007202:Indicators and Reagents; D010084:Oxidation-Reduction; D011284:Pregnenolone / Q000737:chemistry; D012855:Sitosterols / Q000737:chemistry; D013256:Steroids / Q000737:chemistry*; D013464:Sulfuric Acids
D002840:Chromates; D007202:Indicators and Reagents; D012855:Sitosterols; D013256:Steroids; D013464:Sulfuric Acids; D004986:Ether; D003687:Dehydroepiandrosterone; C025473:gamma-sitosterol; D011284:Pregnenolone; D002784:Cholesterol; D003903:Deuterium; D004144:Diosgenin; C033158:sulfuric acid; C034944:chromic acid