Reactions of the K-Region Epoxides of Polycyclic Aromatic Hydrocarbons with Phosphodiesters. A Potential Detoxification Reaction

Article abstract of DOI:10.1021/jo00347a009

Phenanthrene 9,10-oxide reacts with diethyl hydrogen phosphate to give 9-phenanthrol.The reaction was first order in both epoxide and phosphate concentrations, with a pseudo-first-order rate constant k_φ = 6.2e-1 mol^-1Ls^-1.Similarly, chrysene 5,6-oxide on reaction with phosphate opened regiospecifically to give 6-chrysenol.Several anilinium phosphate salts were prepared and reacted with phenanthrene 9,10-oxide.The extent of reaction was markedly influenced by the pK_a of the anilinium salt.The biological implications of this study in understanding the relative noncarcinogenicity of K-region arene oxides are discussed.