SYNTHESIS OF THE DIHYDRODIOLS AND DIOL EPOXIDES OF BENZO[E]PYRENE AND TRIPHENYLENE

Synthesis of the “bay region” dihydrodiols of benzo[e]pyrene and triphenylene (1 and 2) and the corresponding anti isomeric diol epoxides (3 and 4) is described. NMR analysis indicates 1-4 exist preferentially in the diaxial conformation in contrast to the analogous derivatives of the potent carcinogen benzo[a]pyrene shown previously to exist preferentially as the diequatorial conformer. Both 3 and 4, derived from hydrocarbons inactive as carcinogens, are inactive as inhibitors of the ɸX 174 DNA virus, whereas the analogous anti-diol epoxide of benzo[a]pyrene is highly potent in this respect. © 1979, American Chemical Society. All rights reserved.