Dilute aqueous solutions of sodium dodecyl sulfate and sodium hexadecyloxyethyl sulfate catalyze the hydrolysis of a series of 2-(substituted phen0xy)tetrahydropyrans. Rate increases from 15-to 50-fold are observed, depending on the nature of surfactant and substrate. Introduction of a methyl group a t the 1 position of the hexadecyloxyethyl sulfate markedly reduces its catalytic effectiveness. Activation parameters for the surfactantdependent reactions vary nonsystematically from those for the same reactions in 50% dioxane-water or in water. In contrast to the behavior of the anionic surfactants, dodecyltrimethylammonium propanesulfonate and dodecyldimethyl phosphine oxide inhibit the hydrolysis of these substrates.
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