Eliminations from (E)-O-arylbenzaldoximes promoted by tertiary amines in acetonitrile. Effects of aryl substituents, base strength, and leaving group upon the nitrile-forming transition state

Bong-Rae Cho, Kee Dong Kim, Jong Chan Lee, Nam Soon Cho

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Elimination reactions of (E)-O-(2,4-dinitrophenyl)benzaldoximes (1) and (E)-O-picrylbenzaldoximes (2) with R3N in MeCN have been investigated. The reactions are quantitative, producing only benzonitriles and aryloxides. The observation of second-order kinetics, β = 0.43-0.81, and |β1g| = 0.39-0.73 is consistent with an E2 mechanism. For reactions of 1 with R3N in MeCN, the β and ρ values increased significantly with electron-withdrawing aryl substitutents and stronger bases respectively. The corresponding changes in the β and ρ values for 2 were in the same direction but much less. When the leaving group was changed from 2,4-dinitrophenoxide to picrate, however, β increased and ρ decreased. Changes in transition-state parameters with alteration in the reactant structure are interpreted as resulting from variation in a nitrile-forming transition state.

Original languageEnglish
Pages (from-to)6145-6148
Number of pages4
JournalJournal of the American Chemical Society
Issue number18
Publication statusPublished - 1988 Dec 1


ASJC Scopus subject areas

  • Chemistry(all)

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