Abstract
Kinetic deuterium isotope effects were determined for E2 reactions of the compounds C/sub 6/H/sub 5/CD/sub 2/CH/sub 2/X. The values of k/sub H//k/sub D/ with sodium ethoxide in ethanol are in the order Br> OTs> SMe/sub 2/> NMe/sub 3/. A change of base and medium to potassium t-butoxide in t-butyl alcohol increases the isotope effect with the bromide and the tosylate. Experiments with sodium hydroxide in water on the onium salts show no clear pattern. The relation of the present work to other recent studies on the nature of the transition state in E2 reactions is discussed. Some rate constants previously given for 2-(p- acetylphenyl)-ethyldimethylsulfonium bromide are shown to be tn error. An interesting case of anomalous orientation in a Friedel-Crafts acylation is reported. (auth)
Published Version
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