Mechanisms of elimination: The E2 reaction of several p-substituted phenylthiapropyl bromides and the corresponding oxygen analogs in t-butanol containing potassium t-butoxide

Abstract

The rates of the base-catalysed elimination of a series of γ-( p-substituted-phenylthia)propyl bromides and the corresponding oxygen analogues have been determined in t-butanol containing potassium t-butoxide. Although the oxygen compounds react faster than the sulfur counterparts, the p value obtained for the sulfur compounds is larger than that for the oxygen compounds. This difference in reactivity and p-values is discussed in terms of the difference between divalent oxygen and sulfur atoms in their ability to transmit electronic effect to a γ-carbon atom.