title: Synthesis of a novel fluorinated benzo[a]pyrene: 4,5-difluorobenzo[a]pyrene.
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.
authors.affiliation: Environmental Health Research and Testing, Inc., Research Triangle Park, NC 27709.
authors.forename: S C
authors.initials: SC
authors.lastname: Agarwal
authors.forename: G
authors.initials: G
authors.lastname: Lambert
authors.forename: W
authors.initials: W
authors.lastname: Padgett
authors.forename: S
authors.initials: S
authors.lastname: Nesnow
mesh_terms: D001564:Benzo(a)pyrene / Q000737:chemistry* / Q000493:pharmacokinetics; D001580:Benzopyrenes / Q000138:chemical synthesis* / Q000493:pharmacokinetics
chemical_list: D001580:Benzopyrenes; C070973:4,5-difluorobenzo(a)pyrene; D001564:Benzo(a)pyrene