Substituent effects in ring-chain tautomerism of the condensation products of non-racemic 1,2-aminoalcohols with aromatic aldehydes

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Abstract

The condensation of (S)-2-amino-2-phenylethanol or (S)-2-amino-3- phenylpropanol with substituted benzaldehydes in methanol or water led to crystalline products, which proved to exist in CDCl 3 at 300 K as three-component (ring cis-open-ring trans) tautomeric mixtures. The electronic effects of the 2-aryl substituents on the tautomeric equilibria were described by the Hammett equation. Good correlations were found between the equilibrium constants and the Hammett-Brown parameter (σ +) of the substituent X on the 2-phenyl group.

Original languageEnglish
Pages (from-to)2012-2017
Number of pages6
JournalTetrahedron Asymmetry
Volume22
Issue number23
DOIs
Publication statusPublished - Dec 15 2011

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ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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