Substituent effects on the ring-chain tautomerism of 1,3-oxazines

Ferenc Fülöp, László Lázár, Gábor Bernáth, Reijo Sillanpää, Kalevi Pihlaja

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

The aryl substituents at positions 4 and 6 do not exert observable electronic effects on the ring-chain tautomeric ratios of 2,4- or 2,6-diarylsubstituted-tetrahydro-1,3-oxazines. On the other hand, the electronic effect of the 2-aryl substituent is marked: in all eight series studied, the equilibria can be described by the equation log K = ρ{variant} σ+ +log K0, where ρ{variant}+ is the Hammett-Brown constant of the 2-aryl substituents, and ρ{variant} is a constant characteristic of the ring system (=0.75±0.05).

Original languageEnglish
Pages (from-to)2115-2122
Number of pages8
JournalTetrahedron
Volume49
Issue number10
DOIs
Publication statusPublished - Mar 5 1993

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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