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13 C labeled benzo[a]pyrenes and derivatives 3. Benzo[a]pyrene‐4,5‐oxide‐4‐ 13 C and benzo[a]pyrene‐4,5‐oxide‐5‐ 13 C
Author(s) -
Hylarides Mark D.,
Daub Guido H.,
Vanderjagt David L.,
Silverman I. Robert
Publication year - 1983
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580200910
Subject(s) - chemistry , pyrene , oxide , benzo(a)pyrene , yield (engineering) , peroxide , medicinal chemistry , nuclear chemistry , organic chemistry , materials science , metallurgy
The synthesis of benzo[a]pyrene‐4,5‐oxide‐4‐ 13 C and benzo[a]‐pyrene‐4,5‐oxide‐5‐ 13 C from the corresponding 13 C labeled 4,5‐dihydrobenzo[a]‐pyrene‐4,5‐diones is described. Reduction of the quinone with potassium borohydride in freshly distilled peroxide‐free 2‐propanol gave the trans ‐diol which was directly cyclized to the oxide by refluxing with DMF‐DMA in chloroform/OMF. The overall yield of the oxide was 48–53% for the two steps. The requisite quinones were available in five steps from 1,2‐dihydrochrysen‐4(3H)‐one as described in an earlier paper. Overall yield of the oxide from the chrysenone was 27%. 13 C NMR of the labeled oxides in CDCl 3 gave chemical shifts of 56.80 for C 5 and 56.20 for C 4 (δ C from TMS) of benzo[a]pyrene‐4,5‐oxide.