Reaction of (E)-o-arylbenzaldoximes with sodium methoxide in methanol. Effect of leaving group upon nitrile-forming transition state

Bong-Rae Cho, Jinhee Jung, Eun Kyung Ahn

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14 Citations (Scopus)

Abstract

Reactions of (E)-Oarylbenzaldoximes 1-3 with MeONa-MeOH have been studied kinetically. The reactions proceed via competing E2 and SNAr reactions, in which the first step is rate-determining. Although the reactions were strongly influenced by the electronic effect of the β- and O-aryl substituents, they were insensitive to the steric effect of the O-aryl group, except that the SNAr reaction was retarded by the CF3 group of 2. For eliminations from 1-3 promoted by MeONa-MeOH, the kH/kD value increased and the Hammett ρ value decreased with better leaving groups. From these results, the effect of leaving group variation upon the nitrile-forming transition state is assessed.

Original languageEnglish
Pages (from-to)3420-3425
Number of pages6
JournalJournal of the American Chemical Society
Volume114
Issue number9
Publication statusPublished - 1992 Dec 1

ASJC Scopus subject areas

  • Chemistry(all)

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