Enhanced Reactivity of RC≡CZ− (R = H and Cl; Z = O, S, and Se) and the Influence of Leaving Group on the α-Effect in the E2 Reactions
The Journal of Organic Chemistry2010Vol. 75(12), pp. 4212–4217
Citations Over TimeTop 17% of 2010 papers
Abstract
The enhanced reactivity exhibited by six pseudo-alpha-bases, RC[triple bond]CZ(-) (R = H and Cl; Z = O, S, and Se) in gas-phase E2 reactions with ethyl chloride was examined at the G2(+) level. It is found that anomalous reactivity is observed despite the fact that these chalcogen bases do not possess adjacent lone-pair electrons. The influence of the halide leaving groups on the alpha-effect and the origin of the alpha-effect in the E2 reactions of ethyl halides are investigated and discussed.
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