Journal of Organic Chemistry p. 3901 - 3904 (1993)
Update date:2022-08-03
Topics:
Cho, Bong Rae
Jang, Wan Jin
Je, Jong Tae
Bartsch, Richard A.
Elimination reactions of (E)-O-pivaloylbenzaldoximes promoted by Et3N-MeCN, t-BuOK-t-BuOH and t-BuOK-DMSO have been studied kinetically.The reactions produce benzonitrile quantitatively.The reactions are second-order and exhibit substantial values of ρ, β, and kH/kD and an E2 mechanism is evident.The rate of elimination from (E)-O-pivaloylbenzaldoxime increased with base-solvent system variation and gave relative rates of 1, 14.8, and 4.31*104 for Et3N-MeCN, t-BuOK-t-BuOH, t-BuOK-DMSO, respectively.The kH/kD value increased, but the Hammett ρ value increased and then decreased, with this change in the base-solvent system.These results are compared with the predictions of the More O'Ferral-Jencks reaction coordinate diagramm to assess its scope and limitations in the interpretation of the elimination reactions.
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