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13 C labeled benzo[a]pyrenes and derivatives. 2. The synthesis of benzo[a]pyrene‐6‐ 13 C
Author(s) -
Simpson J. Ernest,
Daub Guido H.,
Vanderjagt David L.
Publication year - 1980
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.2580170615
Subject(s) - chemistry , pyrene , dehydrogenation , ketone , yield (engineering) , benzo(a)pyrene , medicinal chemistry , organic chemistry , catalysis , materials science , metallurgy
The synthesis of benzo[a]pyrene‐6‐ 13 C is described. Perinaphthane was converted to 6‐benzoyl‐carbonyl‐ 13 C‐perinaphthane which was cyclized to 2,3‐dihydrobenzo[a]pyren‐6(1H)‐one‐6‐ 13 C. Subsequent reduction of the ketone followed by dehydration and dehydrogenation gave benzo[a]pyrene‐6‐ 13 C in 29% overall yield.