Solvent-dependent competitive rearrangements of cyclic tertiary propargylamine N-oxides

Anna Szabó, Ágnes Galstnibos-Faragó, Zoltán Mucsi, Géza Timári, Lelle Vasvári-Debreczy, István Hermecz

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8 Citations (Scopus)

Abstract

In protic media, cyclic propargylamine N-oxides 1 undergo solvent-dependent competitive rearrangements leading to enamino aldehydes 5, acrylamides 3, and secondary amines 4. The ratios of the products are evaluated and the possible mechanism of the competing reactions is interpreted by reaction kinetics studies and ab initio calculations. (

Original languageEnglish
Pages (from-to)687-694
Number of pages8
JournalEuropean Journal of Organic Chemistry
Issue number4
DOIs
Publication statusPublished - Feb 13 2004

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Keywords

  • Ab initio calculations
  • Reaction mechanisms
  • Rearrangements
  • Solvent effects

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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