Title

Carbon-Oxygen Hydrogen Bonding in Dehydrohalogenation Reactions: PM3 Calculations on Polyhalogenated Phenylethane Derivatives

Document Type

Article

Publication Date

1-1-1997

Abstract

The dehydrohalogenation reactions of PhCH -CH Cl and PhCHCl-CX 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 -CH Cl and PhCHCl-CH 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. 2 2 2 2 2 2

Publication Name

Journal of Organic Chemistry

Volume Number

62

First Page

7457

Last Page

7463

Issue Number

21

DOI

10.1021/jo962154w

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