Circulardichroismus—XXXIX : Synthese und circulardichroismus von einigen β-substituierten adamantanonen—II

Abstract

The synthesis and CD of various optically active β-substituted adamantanones and adamantanediones are described. All “equatorial” substituents obey the octant rule for ketones, whereas the “axial” ones (with the exception of OH) show antioctant behaviour. The “axial” methoxy adamantanone ( 8) gives pronounced fine structure in unpolar solvents, the sign of its CD depends on the solvent used. The vicinal effects of these 1,5-diketones are considerable. A positive charge on a N atom gives an antioctant contribution. Chromophores in the substituents also give rise to CD.