The oxidation of a steroidal bromohydrin revisited

A comparative study was made of the reactions of 5-bromo-3β,6β-dihydroxy-5α-androstan-17-one 3-acetate ($\text{1}$) with lead tetraacetate alone and in the presence of iodine in both high intensity visible light and in total darkenss 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.