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Conformational studies of sterically comparable 2,4-disubstituted bicyclo[3.3.1]nonan-9-one systems

✍ Scribed by Lakshmy Ravishankar; Dinesh N. Rele; Kunnavakam V. Geetha; Hari H. Mathur; Girish K. Trivedi

Publisher
John Wiley and Sons
Year
1987
Tongue
English
Weight
444 KB
Volume
25
Category
Article
ISSN
0749-1581

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✦ Synopsis

Condensation of substituted cyclohexanones with cinnamaldehydes and morpholine in the presence of anhydrous cerium(II1) chloride was carried out. The stereochemistry of the condensed products, variously substituted 2morpholino-4-phenylbicyclo[3.3.l]nonan-9-ones, was deduced by using the 'H NMR COSY technique and 13C NMR data. In order to draw a general conclusion, the stereochemistry of the sterically comparable 2p-diphenylbicyclo[3.3.1]nonan-9-one was also studied in detail, using 'H NMR COSY and 13C NMR data. A general conclusion regarding the boat-chair conformational preference for such sterically comparable cis-2,4-disubstituted bicyclo[3.3.l]nonan-9-ones has been deduced, with the substituted ring in the boat form and a diequatorial disposition of the two substituents.

πŸ“œ SIMILAR VOLUMES

Carbon-13 NMR spectra of solid bicyclo[3
Carbon-13 NMR spectra of solid bicyclo[3. 3. 1]nonan-9-one. Conformational studies in the solid state
✍ Roderick E. Wasylishen; Kenneth J. Friesen πŸ“‚ Article πŸ“… 1980 πŸ› John Wiley and Sons 🌐 English βš– 188 KB

## Abstract Carbon‐13 NMR spectra of solid polycrystalline bicyclo[3.3.1]nonan‐9‐one and adamantanone have been measured at 315K. The relatively narrow ^13^C linewidths observed for these solids, together with measured spin‐lattice relaxation times, indicate that both these solids are orientational