Solid‐state NMR study of the kinetics of a ring chain tautomerism in a tetrahydro‐1, 3‐oxazine derivative

Frank G. Riddell, Martin Rogerson, F. Fülöp, G. Bernáth

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Condensation of cis‐2‐aminomethylcyclohexanol with p‐nitrobenzaldehyde under mild conditions initially gives the imine as the kinetically controlled product. The imine undergoes a solid‐state rearrangement to the bicyclic tetrahydro‐1, 3‐oxazine. The kinetics of the rearrangement were followed by solid‐state CP/MAS 13C NMR spectroscopy over the temperature range 283–297 K and the reaction was shown to have an activation energy of 85.0 ± 14.7 kJ mol−1. The probable reaction mechanism is discussed.

Original languageEnglish
Pages (from-to)600-602
Number of pages3
JournalMagnetic Resonance in Chemistry
Volume33
Issue number7
DOIs
Publication statusPublished - 1995

Fingerprint

Imines
Nuclear magnetic resonance spectroscopy
Condensation
Activation energy
Nuclear magnetic resonance
Derivatives
Kinetics
Temperature

Keywords

  • C NMR
  • kinetics
  • NMR
  • ring chain tautomerism, solid‐state NMR
  • Tetrahydro‐1, 3‐oxazines

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)

Cite this

Solid‐state NMR study of the kinetics of a ring chain tautomerism in a tetrahydro‐1, 3‐oxazine derivative. / Riddell, Frank G.; Rogerson, Martin; Fülöp, F.; Bernáth, G.

In: Magnetic Resonance in Chemistry, Vol. 33, No. 7, 1995, p. 600-602.

Research output: Contribution to journalArticle

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AU - Bernáth, G.

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