Reactions of (E)-O-arylbenzaldoximes with secondary amines in acetonitrile. Competition between E2 and SNAr reactions

Bong-Rae Cho, Byung Kwon Min, Chan Woo Lee, Jong Tae Je

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Abstract

Reactions of (E)-O-arylbenzaldoximes in which the O-aryl group is 2,4-dinitrophenyl (1) and picryl (2) with secondary amines in acetonitrile have been studied kinetically. The reactions proceed via competing E2 and SNAr mechanism. The second rate-determining step of the SNAr reactions involves both uncatalyzed and base-catalyzed pathways. The sensitivity of the SNAr reaction to base catalysis was greater for 2 and increased with base strength. The rates of E2 and SNAr reactions increased by approximately 103 and 104 fold, respectively, with the variation of the substrate from 1 to 2. The yield of SNAr product increased with base concentration, electron-withdrawing ability of O-aryl group, and base strength. From these results, factors that influence the competition between E2 and SNAr reaction pathways are assessed.

Original languageEnglish
Pages (from-to)5513-5517
Number of pages5
JournalJournal of Organic Chemistry
Volume56
Issue number19
Publication statusPublished - 1991 Dec 1

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ASJC Scopus subject areas

  • Organic Chemistry

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