Elimination vs. Substitution in the reaction of 3-Stannyl Esters and 3-Stannyl Nitriles with Sodium tert-Butoxide in DMSO

ALICIA CHOPA,; GUSTAVO SILBESTRI,; MERCEDES BADAJOZ,; ANA PAULA MURRAY

Arkivoc

ARKAT

Año: 2003 vol. 2003 p. 382 - 389

1424-6376

The reaction of 3-stannyl propanoates and 3-stannyl propanonitriles with sodium tert-butoxide in DMSO leads to elimination and/or substitution products. The composition of the product mixture depends on the nature of the ligands attached to tin and also on the nature of the functional group (COOMe or CN). Stereochemical results suggest that the elimination reactions proceed through an (E1cB)R mechanism.tert-butoxide in DMSO leads to elimination and/or substitution products. The composition of the product mixture depends on the nature of the ligands attached to tin and also on the nature of the functional group (COOMe or CN). Stereochemical results suggest that the elimination reactions proceed through an (E1cB)R mechanism.R mechanism.