The consequences of steric effects in the cleavage step of the sulfohaloform reaction

DG Kay, RF Langler…

Index: Kay,D.G. et al. Canadian Journal of Chemistry, 1979 , vol. 57, p. 2185 - 2190

Full Text: HTML

Citation Number: 13

Abstract

The pathway for the aqueous chlorinolysis of a series of β-sulfonyl-sulfides is elucidated and the SN2 cleavage step examined. Steric effects in the cleavage of the α-polychloro- oxochloro-sulfonium chloride intermediates are held to be responsible for the suppression of the established nucleophilic competition between water molecules and chloride ions with the result that all cleavage products arise from nucleophilic attack by chloride ions. This ...