Resolution and Absolute Configuration of K-Region Trans Dihydrodiols from Polycyclic Aromatic Hydrocarbons

Article abstract of DOI:10.1021/jo00360a024

K-region trans dihydrodiols of benzophenanthrene, chrysene, pyrene, and dibenzacridine have been resolved as their diastereomeric diesters with (-)-(menthyloxy)acetic acid, and their absolute configuration have been assigned by the application of circular dichroism and excition chirality methods.For these as well as the K-region trans dihydrodiol derivatives from five other hydrocarbons, a consistent pattern of physical properties has emerged.The R,R diastereomers are less retained on silica gel HPLC columns when eluted with ether-cyclohexane mixtures and show negative values of <α>_D in tetrahydrofuran, the degree of magnetic nonequivalence between H_A and H_B in the -OCH_AH_BCO2- portion of the diesters (100 MHz, C6D6) is generally much higher for the S,S enantiomers of the dihydrodiols, and the free R,R dihydrodiols have positive values of <α>_D in tetrahydrofuran provided their hydroxyl groups do not have a marked preference for the pseudodiaxial conformation.