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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.
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