Metallic samarium promoted reductive dimerization cyclization of gem-diactivated alkenes, reductive debromination of vic-dibromides, and reduction of sodium alkyl thiosulfates in aqueous media

✍ Scribed by Lei Wang; Yongmin Zhang

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 902 KB
• Volume: 55
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(99)00602-x

✦ Synopsis

In saturated NH4CI (aq.)-THF solution at room temperature, metallic samarium promoted reductive dimerization cyclization of gem-diactivated alkenes, reductive debromination of vic-dibromides, and reduction of sodium alkyl thiosulfates occur to afford corresponding functionalized cyclopentenes, (E)-alkenes, and disulfides, respectively in good yield. Only sub-stoichiometric quantities of samarium are employed in the former reactions and the trans-or trans, trans-form isomer is the majority product of the polysubstituted cyclopentene products.