149540-91-0Relevant academic research and scientific papers
Elimination Reactions of (E)-O-Pivaloylbenzaldoximes
Cho, Bong Rae,Jang, Wan Jin,Je, Jong Tae,Bartsch, Richard A.
, p. 3901 - 3904 (2007/10/02)
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.
