64440-29-5Relevant academic research and scientific papers
Resolution and Absolute Configuration of K-Region Trans Dihydrodiols from Polycyclic Aromatic Hydrocarbons
Balani, S. K.,Bladeren, P. J. van,Shirai, N.,Jerina, D. M.
, p. 1773 - 1778 (1986)
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 D in tetrahydrofuran, the degree of magnetic nonequivalence between HA and HB in the -OCHAHBCO2- 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 D in tetrahydrofuran provided their hydroxyl groups do not have a marked preference for the pseudodiaxial conformation.
