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Dehydrohalogenation of ethyl halide

Ahubelem, N., Altarawneh, M.ORCID: 0000-0002-2832-3886 and Dlugogorski, B.Z. (2014) Dehydrohalogenation of ethyl halide. Tetrahedron Letters, 55 (35). pp. 4860-4868.

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Link to Published Version: http://dx.doi.org/10.1016/j.tetlet.2014.07.009
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Abstract

Unimolecular decomposition kinetics of selected ethyl halides, phenethyl halides and methoxyphenethyl halides have been investigated using high level computational chemistry methods. The phenethyl halides decompose faster than the ethyl halides due to a more electronegative chlorine atom, induced by the chloroethyl functionality as an electron-withdrawing group. 1-Chloro-2-(methylthio)ethane exhibits faster dehydrochlorination than that of chloroethane/1-chloro-2-methoxyethane, owing to more polarisable C⋯H and C⋯Cl bonds in the transition structures. Calculations suggest that electronic factors rather than anchimeric assistance influence the dehydrochlorination reactions.

Item Type: Journal Article
Murdoch Affiliation(s): School of Engineering and Information Technology
Publisher: Elsevier BV
Copyright: 2014 Elsevier Ltd
URI: http://researchrepository.murdoch.edu.au/id/eprint/23282
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