Polycyclic aryloxiranes: A new class of carcinogens

Summary Metabolism of carcinogenic hydrocarbons is known to afford K-region and non-K-region oxides, both of which exhibit significant biological activity. Synthesis of a new class of oxide derivatives of polycyclic hydrocarbons, the aryloxiranes, is now described. A series of aryloxiranes and a related series of vinyl analogs were synthesized from the corresponding aldehydes via the Corey and Wittig reactions, respectively. Preliminary tests indicate the oxirane, formyl, and vinyl derivatives of benzo(a)pyrene and benz(a)anthracene to be moderately active carcinogens, while the related derivatives of the naphthalene and anthracene ring systems are inactive.