Preparation and reactions of 3,4-bisstannyl-2(5H)furanones

Bistributylstannyl-2(5H)-furanone has been prepared from 3-(tetrahydropyran-2-yl)oxy but-2-ynoate and shown to exhibit good selectivity in its Stille reactions with a range of halogenated compounds, leading to 4-substituted-3-stannyl-2(5H)-furanones, in generally moderate yield. Under certain reaction conditions, doubly substituted products were also isolated from the reactions. The 3,4-bistrimethylstannyl furanone, , corresponding to was prepared, but decomposed during all attempts to execute Stille reactions upon it.