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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Dimethyl Sulfoxide
benzonitrile

ASJC Scopus subject areas

  • Organic Chemistry

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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.

Elimination reactions of (E)-O-pivaloylbenzaldoximes. / Cho, Bong-Rae; Jang, Wan Jin; Je, Jong Tae; Bartsch, Richard A.

In: Journal of Organic Chemistry, Vol. 58, No. 15, 01.12.1993, p. 3901-3904.

Research output: Contribution to journalArticle

Cho, B-R, Jang, WJ, Je, JT & Bartsch, RA 1993, 'Elimination reactions of (E)-O-pivaloylbenzaldoximes', Journal of Organic Chemistry, vol. 58, no. 15, pp. 3901-3904.
Cho B-R, Jang WJ, Je JT, Bartsch RA. Elimination reactions of (E)-O-pivaloylbenzaldoximes. Journal of Organic Chemistry. 1993 Dec 1;58(15):3901-3904.
Cho, Bong-Rae ; Jang, Wan Jin ; Je, Jong Tae ; Bartsch, Richard A. / Elimination reactions of (E)-O-pivaloylbenzaldoximes. In: Journal of Organic Chemistry. 1993 ; Vol. 58, No. 15. pp. 3901-3904.
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