Conformational studies of N(3)-substituted [1,3,4]-oxadiazinan-2-ones

Pseudoephedrine-based [1,3,4]-oxadiazinan-2-ones acylated at the N(3)-position with either acetyl (2a), propionyl (2b), or phenylacetyl (2c) substituents are known to undergo conformational changes that are observable by (13)C NMR spectroscopy. The conformational properties of new [1,3,4]-oxadiazina...

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Bibliographic Details
Published in:Journal of organic chemistry 2002-12, Vol.67 (25), p.8871-8876
Main Authors: Casper, David M, Blackburn, Jennifer R, Maroules, Christopher D, Brady, Tana, Esken, Joel M, Ferrence, Gregory M, Standard, Jean M, Hitchcock, Shawn R
Format: Article
Language:English
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Summary:Pseudoephedrine-based [1,3,4]-oxadiazinan-2-ones acylated at the N(3)-position with either acetyl (2a), propionyl (2b), or phenylacetyl (2c) substituents are known to undergo conformational changes that are observable by (13)C NMR spectroscopy. The conformational properties of new [1,3,4]-oxadiazinan-2-one derivatives 2d-k are examined by X-ray crystallography and variable-temperature (13)C NMR spectroscopy and further evaluated by semiempirical AM1 calculations. The collected data reveal that the conformational changes of the overall ring system are dependent upon the stereoelectronic factors of the N(3)-substituent.
ISSN:0022-3263