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© 1991 Oxford University Press

research-article

Synthesis of a novel fluorinated benzo[a]pyrene: 4,5-difluorobenzo [a] pyrene

Satish C. Agarwal, Guy Lambert, William Padgett and Stephen Nesnow 1 1

Environmental Health Research and Testing, Inc., Research Triangle Park, NC 27709 Health Effects Research Laboratory, US Environmental Protection Agency Research Triangle Park, NC 27711, USA
1Carcinogenesis and Metabolism Branch, Health Effects Research Laboratory, US Environmental Protection Agency Research Triangle Park, NC 2771 1, USA

The synthesis of 4,5-difluorobenzo[a]pyrene, as a fluorinated probe to investigate the involvement of the K-region in the further metabolic activation of benzo[a]pyrene metabolites, is described. Benzo[a]pyrene-4,5-dione obtained from 2,3-dichloro-5,6-dicyano-1,4-benzoquinone oxidation of cis-4,5-dihydro-4,5-dihydroxybenzo[a]pyrene was fluorinated with dimethylaminosulfur trifluoride to give 4H,5H,4,4,5,5,-tetrafluorobezo[a]pyrene. Defluorination using lithium aluminum hydride in tetrahydrofuran gave 4,5,-difluorobenzo[a]pyrene.


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