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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Abstract

Reactions of (E)-O-arylbenzaldoximes 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)3425-3429
Number of pages5
JournalJournal of the American Chemical Society
Volume114
Issue number9
DOIs
Publication statusPublished - 1992 Apr 1

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Nitriles
Methanol
Sodium

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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Reaction of (E)-O-Arylbenzaldoximes with Sodium Methoxide in Methanol. Effect of Leaving Group upon Nitrile-Forming Transition State. / Cho, Bong-Rae; Jung, Jinhee; Ahn, Eun Kyung.

In: Journal of the American Chemical Society, Vol. 114, No. 9, 01.04.1992, p. 3425-3429.

Research output: Contribution to journalArticle

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