Channeling the SmI₂ reactions to the radical path: Radicals resisting reduction by SmI₂

Studies on the reaction of 4-(2,2-diphenylvinyl)pyridine with SmI ₂ revealed that the intermediate radical strongly resists further reduction to the corresponding anion. The resistance of the radical to accepting another electron is traced to its stabilization by the nitrogen lone pair. The literature suggests that oxygen may also play a role similar to that of nitrogen in directing the course of the reaction toward radical rather than to anionic chemistry.