Dehydrohalogenation of ethyl halides

Nwakamma Ahubelem, Mohammednoor Altarawneh, Bogdan Z. Dlugogorski

Research output: Contribution to journalArticle

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.

Original languageEnglish
Pages (from-to)4860-4868
Number of pages9
JournalTetrahedron Letters
Volume55
Issue number35
DOIs
Publication statusPublished - 27 Aug 2014
Externally publishedYes

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Ahubelem, N., Altarawneh, M., & Dlugogorski, B. Z. (2014). Dehydrohalogenation of ethyl halides. Tetrahedron Letters, 55(35), 4860-4868. https://doi.org/10.1016/j.tetlet.2014.07.009