Ring-chain tautomerism of 1,3-oxazolidines prepared from norephedrine and norpseudoephedrine

Ferenc Fülöp, Gábor Bernáth, Jorma Mattinen, Kalevi Pihlaja

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50 Citations (Scopus)

Abstract

The reactions of norephedrine and norpseudoephedrine with eleven different aromatic aldehydes led, in each case, to tautomeric equilibria consisting of two ring and one open-chain forms and obeying the equation: log Kx = ρ{variant}σ+ + c, where ρ{variant} = 0.54±0.02 and 0.53±0.02 and c = -0.36±0.02 and +0.34±0.02, respectively. A connection was also found between the stereoselectivity of the ring-closures and the Hammett σ+ constants.

Original languageEnglish
Pages (from-to)4317-4324
Number of pages8
JournalTetrahedron
Volume45
Issue number13
DOIs
Publication statusPublished - 1989

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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