NEIGHBORING TIN EFFECT IN THE OXIDATION OF ALPHA-STANNYL PHENYL VINYLSULFIDES

alpha-Stannyl vinyl sulfides were generally prepared by hydrostannylat ion of thioacetylenes catalyzed by Pd(PPh3)(4). The regio-and stereoch emistry of the products was determined unequivocally in three cases by X-ray crystallographic structure studies and in the others by H-1 NMR spectroscopic analysis. The irreversible oxidation potentials of thes e compounds were determined in acetonitrile and dichloromethane by cyc lic voltammetry. The oxidation potentials provide evidence for signifi cant interaction between the C-Sn sigma bond and sulfur 3p lone pair o rbital in cases with appropriate geometry. (C) 1997 Elsevier Science L td.