The synthesis of 10‐fluorobenzo[a]pyrene

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Abstract
The synthesis of 10‐fluorobenzo[a]pyrene in four steps from 11‐fluoro‐12‐methylbenz[a]anthracene is described.A current hypothesis concerning the metabolism which is responsible for the carcinogenic activity of benzo[a]pyrene, BP, maintains that BP is converted into isomers of 7,8‐dihydroxy‐9,10‐epoxy‐7,8,9, 10‐tetrahydrobenzo[a]pyrene which are the true carcinogens.1 If any of 7‐,8‐,9‐, and 10‐fluorobenzo[a]pyrenes proved carcinogenic an alternate mechanism for carcinogenesis would be required. If all four fluorinated compounds were non‐carcinogenic strong support of the current hypothesis would be provided.2 Accordingly we planned to synthesize the fluoro BP compounds so that adequate testing could be carried out.

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