The Reaction of (Arylthio)trimethylstannanes with 1-Aryl-1-bromoethanes: Effect of Substituent on the Process Shifting from Unimolecular to Bimolecular Substitution

Article abstract of DOI:10.1246/bcsj.64.2407

A kinetic study has been conducted on the reaction of (arylthio)trimethylstannanes with 1-aryl-1-bromoethanes.The reaction of the arylbromoethane bearing an electron-donating substituent was found involving unimolecular ionization of the arylbromoethane.The other reactions, however, were found to be second-order reactions.The nature of the second-order reactions was shifted from one involving unimolecular ionization as the minor process, to a clear bimolecular nucleophilic reaction, according to the electron-withdrawing nature of the substituents on the arylbromoethanes.