Journal of Organic Chemistry p. 8028 - 8035 (1995)
Update date:2022-07-29
Topics:
Usuki, Yoshinosuke
Wang, Yuguang
Aube, Jeffrey
The 1H NMR spectra of spirocyclic oxaziridines derived from substituted cyclohexanones and benzylamines were studied.Depending on substitution and on stereochemistry, these compounds often exhibit a substantial upfield shift of the cyclohexyl methylene or methine protons with a 1,3-diaxial relationship to the oxaziridine N-substituent.This effect is ascribed to a conformation that places an aromatic group over the plane of the cyclohexane ring.This conformation has also been found in the solid state by X-ray crystallography and is supported by molecular mechanics calculations.The use of the effect in assigning stereochemistry to this series of compounds is discussed.
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