The various roles of the lone pair in the conformational dynamics and preferences of medium heterocycles are not clearly defined (11, although certain cases seem clear, e.g., the "E-axial effect" (2).
Half-chair conformations of unsaturated heterocyclic compounds
β Scribed by D. M. Fatheree; G. L. Deeg; D. B. Matthews; J. G. Russell
- Book ID
- 102950902
- Publisher
- John Wiley and Sons
- Year
- 1982
- Tongue
- English
- Weight
- 535 KB
- Volume
- 18
- Category
- Article
- ISSN
- 0749-1581
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β¦ Synopsis
Abstract
The vicinal proton coupling constants were obtained for some 6βmembered ring unsaturated heterocyclic compounds. The R values and ring dihedral angles were determined and found to be consistent with halfβchair conformations. Relative to saturated heterocyclic compounds, the effect of the sulfur atom on ring puckering was attenuated. However, an increase in ring puckering resulted from the sulfone group and was attributed to torsional energy.
π SIMILAR VOLUMES
We have previously (2) described an unusual type of conformational preference effect vhich vaa found to operate in ring A of some 3-substituted (-OH and -N3), A 5(10) -steroids. From the RMR spectra of these epimer pairs in the C-3 proton region, It was evident that the 3a-and