Synthesis, Stereoselective Reactions, and Reactivity of 9-Triptycyldimethyltin Hydride

Abstract

The synthesis of the new compounds 9-triptycyldimethyltin bromide (2) and 9-triptycyldimethyltin hydride (3) and some of their physical properties are described. The radical addition of 3 to methyl (E)-2,3-diphenylpropenoate gave the threo adducts as the only products. The results obtained in the addition of hydride 3 to mono- and disubstituted alkynes under radical and palladium-catalyzed conditions indicate that these reactions take place with high stereoselectivity. The chemical reactivity of these vinylstannanes is similar to that of vinyltriorganostannanes containing smaller organic ligands. Full 1H, 13C, and 119Sn NMR characteristics are included.