ELUCIDATION OF THE STEREOCHEMISTRY OF TA-(9.10-DIHYDROANTHRACENE-9,10-DIYL)-SUCCINIMIDES BY H-1-NMR SPECTROSCOPY

Syn configuration of N-arylaldimines has been demonstrated with the he lp of an asymmetric cage moiety. H-1 NMR spectral studies of eta-(9,10 -dihydroanthracene-9,10-diyl)succinimides have shown restricted rotati on about N-N bond and the aldimino group orthogonal to the succinimidy l plane. The repulsive interaction of sp(2) - nitrogen lone electron p air from the phenyl ring of the cage has been attributed to the stabil ity of the hydrazone. The orthogonal geometry of the aldimino group ha s been further substantiated by the formation of a six membered intram olecular chelate ring with the 2'-OH/-NH2 substituent in the aryl grou p.