COTTON EFFECT OF DIMEDONE CONDENSATION COMPOUNDS WITH OPTICALLY ACTIVE AMINES

The Cotton effect of dimedone condensation products of several optically active aliphatic, alicyclic, and aromatic amines was examined by rotatory dispersion and circular dichroism techniques. A correlation has been established between the sign of the Cotton effect and the absolute configuration of the asymmetric center under investigation. All dimedonyl derivatives of aliphatic and alycyclic amines investigated in this study having the (R) configuration exhibit a positive Cotton effect in the 280 mμ region. A negative Cotton effect is observed for compounds showing the (S) configuration. The hydrochlorides of some dimedonyl derivatives were prepared. The sign of the Cotton effect is the same as in the free base. Solvent-dependent equilibria were noted. © 1968.