Dibenzyl diselenide

UsesDibenzyl diselenide is used as a source of the PhSe unit in organic synthesis. It is also used to introduce PhSe groups by reaction with a variety of nucleophilic, including enolates, enol silyl ethers, Grignard reagents, organolithium reagents, alkenes and amines.

PreparationDibenzyl diselenide was synthesized from bis(methoxymagnesium) diselenide reagent as reported by Gunther using benzyl chloride (6.3 g, 0.05 mole) and a methanolic solution of bis(methoxymagnesium) diselenide reagent (from 0.05 gatom of selenium). After 10 min stirring, water (100 mL) and concentrated hydrochloric acid (5 mL) were added, the solution was cooled, and the black solid was collected by filtration. This black solid was then extracted with ethanol to yield a bright yellow solution which, upon solvent removal, gave a yellow crystalline product. The 1H NMR of the yellow solid (in CDCl3) was identical to that of commercially available dibenzyl diselenide.