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