The proposed research has as its initial objective development of a new synthetic approach to K-region oxidized derivatives of polycyclic hydrocarbons not subject to the deficiencies of existing methods in order to make these compounds available in adequate quantities for further research. The dihydroaromatic molecules obtained through metal-ammonia reduction of the parent hydrocarbons (following procedures developed earlier in this laboratory) will be oxidized directly to the corresponding K-region quinones, then further transformed to the dihydrodiols, K-region epoxides, and phenols. Where two isomeric phenols are possible, both will be synthesized. In the second phase of the work it is intended to investigate the chemical properties of the arene oxides, dihydrodiols, and phenols with attention to processes potentially involved in the intimate mechanism of carcinogenesis. These include: (1) the tautomeric equilibrium between the keto and enol forms of the aromatic phenols; (2) rearrangement of arene oxides to phenols, oxepins, etc.; (3) dehydration and accompanying unknown reactions of dihydrodiols; and (4) reactions of K-region oxides with mild nucleophilic reagents, models for attack by cellular components. The results of the foregoing will be assessed in the light of a proposed theory relating carcinogenicity to chemical reactivity in the K-region as a function of polarization of the epoxide function. BIBLIOGRAPHIC REFERENCES: W. M. Baird, R. G. Harvey, and P. Brookes. Comparison of the Cellular DNA-bound Products of Benzo (a) pyrene with the Products Formed by the Reaction of Benzo (a) pyrene 4,5-oxide with DNA. Cancer Res., 35, 54 (1975). H. Cho, R. G. Harvey, and P. W. Rabideau. 9-Isopropylidene-9,10-dihydroanthracene. Synthesis, Stereochemistry, and the Effect of 10-Alkyl Group Size on the Equilibrium with 9-Isopropyl-10-alkyl-anthracene. J. Amer. Chem. Soc., 97, 1140 (1975).