The oxidation of a steroidal bromohydrin revisited.
A comparative study was made of the reactions of 5-bromo-3 beta, 6 beta-dihydroxy-5 alpha-androstan-17-one 3-acetate (1) with lead tetraacetate alone and in the presence of iodine in both high intensity visible light and in total darkness using a variety of solvents. Markedly different product profiles were obtained under the different reaction conditions, making our results of both practical importance and theoretical interest.
D000732:Androstanols; D055598:Chemical Phenomena; D002621:Chemistry; D007455:Iodine; D007854:Lead; D008027:Light; D009682:Magnetic Resonance Spectroscopy; D009942:Organometallic Compounds; D010084:Oxidation-Reduction; D013257:Steroids, Brominated
D000732:Androstanols; D009942:Organometallic Compounds; D013257:Steroids, Brominated; D007854:Lead; C029434:5-bromo-3,6-dihydroxyandrostan-17-one-3-acetate; D007455:Iodine; C029433:lead tetraacetate