Mechanisms of elimination reactions. Part III. Rate coefficients for elimination from substituted 2-phenylethyl arenesulphonates with potassium in t-butyl alcohol
- 1 January 1971
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society B: Physical Organic
- p. 498-502
- https://doi.org/10.1039/j29710000498
Abstract
The rate coefficients for elimination from 24 substrates in the series 2-Z-phenylethyl p-Y-arenesulphonate with potassium t-butoxide in t-butyl alcohol at 40 °C have been correlated with the Hammett equation. The reaction constants ρz decrease linearly with the electronic properties of the group Y only for the most electron-withdrawing substituents, indicative of a shift to transition states with less carbanion character. The reaction constants ρY become less positive as Z becomes more electron-withdrawing, suggesting that increased Cβ–H bond breaking is accompanied by decreased Cα–X bond breaking, and a shift to a transition state with greater carbanion character. This result supports earlier secondary deuterium isotope studies in establishing a new interpretation of the reactivity ratio kOTs/kBr as a measure of C–X bond breaking.Keywords
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