Reductive cleavage of the Se–Se bond in diselenides by the Sm/HgCl₂ system: Formation and reactions of samarium selenolates

Treatment of diaryl diselenides and dialkyl diselenides with metallic samarium and mercury (II) chloride in tetrahydrofuran conveniently gave samarium arylselenolates and alkylselenolates. These “living” species reacted with acyl chlorides, acid anhydrides, methyl chloroformate, organic halides, epoxides, α,β-unsaturated esters, and an α,β-unsaturated nitrile to afford selenoesters, selenoformates, and unsymmetrical selenides in good yields under mild and neutral condition. © 1999 John Wiley & Sons, Inc. Heteroatom Chem 10: 203–208, 1999