The Photo-induced Radical Rearrangement of 7-Oxocholesteryl Hypoiodite in the Presence of Mercury(II) Oxide and Iodine

Article abstract of DOI:10.1246/bcsj.55.517

7-Oxocholesteryl hypoiodite in benzene containing mercury(II) oxide and iodine underwent a photo-induced rearrangement to give 5-iodomethyl-A-nor-5ξ-cholestane-3,7-dione and 2-iodo-7-oxo-A-nor-2,3-secocholest-5-en-3-yl formate in low yields, together with cholesta-3,5-dien-7-one without any accompanying 3α,5-epoxy-6-iodo-A-homo-4-oxacholestanes which are common products in the reactions of cholest-5-en-3-ols.The results thus show that the introduction of an oxo group at the C-7 position results in an appreciable change in the products of the reactions of cholest-5-en-3-ols.