Abstract
The dehydrohalogenation reactions of PhCH(2)-CH(2)Cl and PhCHCl-CX(2)LG (X = H, F; LG = F, Cl) with methoxide have been studied using PM3 quantum chemical calculations in vacuo and within a dielectric medium. For PhCH(2)-CH(2)Cl and PhCHCl-CH(2)Cl the loss of HCl is predicted to occur via an E2 mechanism, while for the other three compounds loss of hydrogen halide occurs via a two-step mechanism, with a hydrogen-bonded carbanion as an intermediate. The mechanistic implications of these calculations are discussed in comparison with experimental data.
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