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260 J. Am. Chem. SOC.1986, 108, 260-269 of BaP and 6-CH3-BaPas reported above are seen to parallel the
 

Summary: 260 J. Am. Chem. SOC.1986, 108, 260-269
of BaP and 6-CH3-BaPas reported above are seen to parallel the
behavior of anthracene. The observed cation radical from BaP
is found to be the 6-CF3C02-BaPcation radical formed most
probably by the following sequence of steps (eq 2). The ap-
-le- CF$202- -le-
BaP -BaP+. -6-CF3C02-BaP--c
6-CF3C02-BaP+.(2)
pearance of a single major product in the HPLC separation of
the reaction prod~cts,~due to the 6-(trifluoroacetoxy)benzo[a]-
pyrene, is further proof of the identity of the observed cation
radical. A similar reaction pathway has been previouslyproposed1*
for the reaction of BaP with manganic acetate in acetic acid in
which the major product is 6-acetoxybenzo[a]pyrene.
6-CH3-BaPis much less reactive in TTFA/TFA; the substi-
tution of the methyl group in the position of highest electron
density considerably retards the substitution reactions, the one-
electron oxidation product of 6-CH3-BaPbeing relatively stable
for several hours at reduced temperatures. Reaction is not,
however, completely elminated; the 6-CH3-BaPf. EPR spectrum

  

Source: Apeloig, Yitzhak - Department of Chemistry, Technion, Israel Institute of Technology

 

Collections: Chemistry