Solvent-mediated allylation of carbonyl compounds with allylic stannanes

The ground state structure of allyltrimethylstannane and tetraallytin in different solvents was analyzed by nuclear magnetic resonance (NMR) to characterize the solvent-mediated allylation of carbonyl compounds. NMR analysis of the ground state structures of tetraallytin and allyltrimethystannane indicated the presence of an intermediate solvent-stabilized ion-pair species during the isomerization of allylic stannanes. The reaction of the tetraallytin was also accelerated in methanol which formed a hydrogen bond with the carbonyl compound.