Abstract
In connection with hydrogen participation in solvolysis, 3-methyl-2-butyl p-toluenesulfonate is a marginal system. Comparison of the behavior of 3-D-3-methyl-2-butyl toluenesulfonate with that of the undeuterated analog discloses a substantial isotope effect on solvolysis rate, but only a small effect on product composition. The evidence points to a relatively high value of ( k Δ/ k s ), the ratio of rate constants for anchimerically assited and unassisted solvolysis processes. Conformational considerations make understandable the relatively low degree of rate acceleration displayed by 3-methyl-2-butyl toluenesulfonate.
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