Title: Secondary α-deuterium kinetic isotope effects for the E2 reaction of the 2-phenylethyl halides with <i>tert</i>-butoxide ion in <i>tert</i>-butyl alcohol
Abstract:Secondary α-deuterium kinetic isotope effects have been determined for the elimination reactions of 2-phenylethyl halides with tert-butoxide in tert-butyl alcohol at 40 °C in the presence and absence ...Secondary α-deuterium kinetic isotope effects have been determined for the elimination reactions of 2-phenylethyl halides with tert-butoxide in tert-butyl alcohol at 40 °C in the presence and absence of the crown ether 18C6. The second-order rate constant k 2 and the normal (k H /k D ) α effect remained constant when the tert-butoxide concentration was varied for reaction of the iodo and bromo compounds. However, both the magnitude of k 2 and the secondary α-deuterium isotope effect were significantly dependent on [t-BuO − ] when chlorine and fluorine are the leaving groups. It is noteworthy that (k H /k D ) α is inverse for the reaction of both the chloro and fluoro compounds at "low" base concentrations and normal at "high" base concentrations. These results are discussed in terms of both syn- and anti-elimination pathways promoted by various associated and dissociated base species. It is suggested that the (k H /k D ) α effect may be useful as a criterion for determining the stereochemistry of E2 elimination reactions.Read More
Publication Year: 1985
Publication Date: 1985-01-01
Language: en
Type: article
Indexed In: ['crossref']
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Cited By Count: 1
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