ON THE REGIOSELECTIVITY IN TRANSFORMATION OF BENZO[A]PYRENE 4,5-OXIDEAND 3-METHYLCHOLANTHRENE 11,12-OXIDE TO THE CORRESPONDING BETA-AMINO-ALCOHOL DERIVATIVES

beta-Amino-alcohol derivatives of benzo[a]pyrene and 3-methylcholanthr ene, 8, 9 and 15 which are assumed to take part in the transformation of the K-region oxides 1 and 10 to the corresponding arene imines, hav e been prepared. The sequence of reactions consists of nucleophilic ox irane ring opening of the epoxides by azide ion, acetylation of the se parated isomeric trans-azido alcohols so formed, and palladium catalyz ed hydrogenation of the resulting beta-acetyloxy azides under ambient conditions. The ratios between the isomeric azido-hydrins obtained fro m 1 and 10, as well as the product distribution in azide-induced oxira ne ring cleavage in other carbocyclic and heterocyclic arene oxides ha ve been shown to correlate with Huckel-type calculations of Wheland's pi-localization energies.