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

✍ Scribed by Frank G. Riddell; Martin Rogerson; Ferenc Fülöp; Gábor Bernáth

Publisher: John Wiley and Sons
Year: 1995
Tongue: English
Weight: 237 KB
Volume: 33
Category: Article
ISSN: 0749-1581
DOI: 10.1002/mrc.1260330719

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✦ Synopsis

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 ^13^C 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.

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