A solid-state NMR study of ring-chain tautomerism in 1,3-O,N-Heterocycles

Frank G. Riddell, S. Arumugam, Ferenc Fülöp, Gábor Bernáth

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22 Citations (Scopus)

Abstract

The solid-state 13C CP/MAS nmr spectra of nineteen tetrahydrooxazines and oxazolidines have been recorded to determine their preferences for the ring or chain tautomeric form in the solid state. The chain form is preferred for those cases in which <80% of the ring tautomer is found in solution. The ring form is exclusively found only in derivatives with ≫93% preference for the ring tautomer in solution. In one case the solid-state reaction converting the open chain to the ring was observed to take place over a time-scale of several days. An investigation of the tautomeric equilibrium in tetrahydrooxazines and oxazolidines in the solid state is reported.

Original languageEnglish
Pages (from-to)4979-4984
Number of pages6
JournalTetrahedron
Volume48
Issue number23
DOIs
Publication statusPublished - Jun 5 1992

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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