Elimination Reactions of (E)-2,4-Dinitrobenzaldehyde O-Aryloximes Promoted by RO-/ROH Buffers in EtOH

Bong Rae Cho, Nam Soon Cho, Kyung Sun Song, Ki Nam Son, Yong Kwan Kim

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Elimination reactions of (E)-2,4-dinitrobenzaldehyde O-aryloximes 1-3 promoted by EtO-, PhC(CH3)=NO-/PhC(CH3)=NOH, and CF3CH2O-/CF3CH3OH buffers in ethanol have been studied kinetically. The reactions produced 2,4-dinitrobenzonitrile and aryloxides as the only products. The observed second-order kinetics, Brønsted β= 0.55-0.75, |β1g| = 0.39-0.48 are consistent with the E2 mechanism. The Brønsted β decreased as the leaving group was made more nucleofugic and the |β1g| increased with a weaker base. The result can be described by a positive interaction coefficient, pxy = ∂β/∂pK1g = ∂β1g/∂pKBH > 0, which provides additional support for the E2 mechanism.

Original languageEnglish
Pages (from-to)3006-3009
Number of pages4
JournalJournal of Organic Chemistry
Volume63
Issue number9
Publication statusPublished - 1998 May 1

ASJC Scopus subject areas

  • Organic Chemistry

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