Elimination reactions of (E)-2,4-dinitrobenzaldehyde O-benzoyloximes promoted by R2NH/R2NH2 + in 70 mol % MeCN(aq). Change of reaction mechanism

Yong Pyun Sang, Bong-Rae Cho

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Abstract

(Chemical Equation Presented) Elimination reactions of (E)-2,4-(NO 2)2C6H3CH=NOC(O)-C6H 4X (1) promoted by R2NH/R2NH2 + in 70 mol % MeCN(aq) have been studied kinetically. The reactions are second-order and exhibit Brönsted β = 0.27-0.32 and |βlg| = 0.28-0.32. The result can be described by a negligible Pxy interaction coefficient, pxy = ∂β/ ∂pKlg = ∂βlg/∂pKBH ≈ 0, which describes the interaction between the base catalyst and the leaving group. The negligible pxy coefficients are consistent with the (E1cb) irr mechanism.

Original languageEnglish
Pages (from-to)9451-9453
Number of pages3
JournalJournal of Organic Chemistry
Volume73
Issue number23
DOIs
Publication statusPublished - 2008 Dec 5

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ASJC Scopus subject areas

  • Organic Chemistry

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