Oxygen atom transfer from iodylbenzene to diphenyl diselenide - a convenient method for dehydrogenation of steroidal 3-ketones

Abstract

Steroidal 3-ketones are smoothly dehydrogenated in high yield using benzeneseleninic anhydride generated in situ by oxygen atom transfer from iodylbenzene, PhIO₂, to catalytic amounts of diphenyl diselenide; use of meta-iodylbenzoic acid in the above cycle has led to the development of an economical and experimentally convenient method avoiding chromatographic separations and with recovery of the m-iodobenzoic acid and the diphenyl diselenide.