Conformational Studies of Sterically Comparable 2,4-Disubstituted Bicyclononan-9-one Systems

Article abstract of DOI:10.1002/mrc.1260251107

Condensation of substituted cyclohexanones with cinnamaldehydes and morpholine in the presence of anhydrous cerium(III) was carried out.The stereochemistry of the condensed products, variously substituted 2-morholino-4-phenylbicyclo(3.3.1)nonan-9-ones, was deduced by using the 1H NMR COSY technique and 13CNMR data.In order to draw a general conclusion, the stereochemistry of the sterically comparable 2,4-diphenyl-bicyclo(3,3,1)nonan-9one was also studied in detail, using 1H NMR COSY and 13C NMR data.A general conclusion regarding the boat-chair conformational preference for such sterically comparable cis-2,4-disubstituted bicyclo(3.3.1)nonan-9-ones has been deduced, with the substituted ring in the boat form and a diequatorial disposition of the two substituents.KEY WORD - Cyclohexanone-cinnamaldehyde condensation 2,4-Disubstituted bicyclo(3.3.1)nonan-9-ones Conformational analysis Application of 1H homo-COSY