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8253706 
Journal Article 
Resolution and Absolute Configuration of K-Region Trans Dihydrodiols from Polycyclic Aromatic Hydrocarbons 
Balani, SK; Van Bladeren, PJ; Shirai, N; Jerina, DM 
1986 
Yes 
Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904 
AMER CHEMICAL SOC 
WASHINGTON 
51 
10 
1773-1778 
English 
WOS:A1986C470000024 
K-region trans dihydrodiols of benzo[c]phenanthrene, chrysene, pyrene, and dibenz[c,h]acridine have been resolved as their diastereomeric diesters with (−)-(menthyloxy)acetic acid, and their absolute configurations have been assigned by the application of circular dichroism and exciton 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 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 [α]D in tetrahydrofuran provided their hydroxyl groups do not have a marked preference for the pseudodiaxial conformation. © 1986, American Chemical Society. All rights reserved.