Selective Formation of α-Cleavage Cycloadduct of Oxirane with Heterocumulene Promoted by High-Coordinated Trialkyltin Complexes

Article abstract of DOI:10.1246/bcsj.64.2661

In the reaction of monosubstituted oxiranes and heterocumulenes, trialkyltin iodides coordinated by phosphine oxides effectively catalyzed the formation of heterocyles via cleavage at the substituted site in the oxirane ring, while other types of organotin complexes or noncomplexed organotin iodides promoted selective cleavage at the opposite site.A mechanistic investigation demonstrated that the coordination of phophine oxide promotes the reverse reaction of the oxirane-ring cleavage leading to the predominant formation of α-cleavage cycloadducts.