L. Ravishankar et al., CONFORMATIONAL STUDIES OF STERICALLY COMPARABLE 2,4-DISUBSTITUTED BICYCLO[3.3.1]NONAN-9-ONE SYSTEMS .2., Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry, 35(1), 1996, pp. 1-4
Condensation of cyclohexanone with cinnamaldehyde and morpholine in th
e presence of anhydrous CeCl3 results in the formation of two isomers
of 2-morpholino-4-phenylbicyclo[3.3.1]nonan-9-one, besides two other p
roducts. The stereochemistry of the minor isomer has been determined w
ith the help of H-1 NMR, COSY, C-13 NMR techniques and H-1 shift reage
nt studies on sterically comparable 2,4-diphenyl-bicyclo[3.3.1]nonan-9
-one. In this case the molecule exists in a twin-chair conformation wi
th the two substituents diequatorially oriented.