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

✍ Scribed by Lei Wang; Yongmin Zhang

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 137 KB
• Volume: 10
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/(sici)1098-1071(1999)10:3<203::aid-hc5>3.0.co;2-p

✦ Synopsis

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, ␣,b-unsaturated esters, and an ␣,b-unsaturated nitrile to afford selenoesters, selenoformates, and unsymmetrical selenides in good yields under mild and neutral condition.