Elimination reactions of (E)-O-pivaloylbenzaldoximes

Bong-Rae Cho, Wan Jin Jang, Jong Tae Je, Richard A. Bartsch

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Abstract

Elimination reactions of (E)-O-pivaloylbenzaldoximes promoted by Et 3N-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 k H/k D 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 × 10 4 for Et 3N-MeCN, t-BuOK-t-BuOH, t-BuOK-DMSO, respectively. The k H/k D 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'Ferrall-Jencks reaction coordinate diagram to assess its scope and limitations in the interpretation of the elimination reactions.

Original languageEnglish
Pages (from-to)3901-3904
Number of pages4
JournalJournal of Organic Chemistry
Volume58
Issue number15
Publication statusPublished - 1993 Dec 1

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ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Cho, B-R., Jang, W. J., Je, J. T., & Bartsch, R. A. (1993). Elimination reactions of (E)-O-pivaloylbenzaldoximes. Journal of Organic Chemistry, 58(15), 3901-3904.