Synthesis of a novel fluorinated benzo[a]pyrene: 4,5-difluorobenzo[a]pyrene |
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Authors: | S C Agarwal G Lambert W Padgett S Nesnow |
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Affiliation: | Environmental Health Research and Testing, Inc., Research Triangle Park, NC 27709. |
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Abstract: | 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,-tetra-fluorobenzo[a]pyrene. Defluorination using lithium aluminum hydride in tetrahydrofuran gave 4,5,-difluorobenzo[a]pyrene. |
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