TY - JOUR
T1 - Regioselectivity in the Controversial Scholl Reaction of 1-Benzoylpyrene
T2 - Formation of a Five-Member Ring Is Not Unexpected
AU - Oded, Yaacov Netanel
AU - Pogodin, Sergey
AU - Agranat, Israel
N1 - Publisher Copyright:
© 2016 American Chemical Society.
PY - 2016/11/18
Y1 - 2016/11/18
N2 - Intramolecular Scholl reaction of 1-benzoylpyrene (1) gave 8H-dibenzo[def,qr]chrysen-8-one (2) and 11H-indeno[2,1-a]pyren-11-one (3) in a 1:2 ratio. The structures of 2 and 3 were determined, using 1H NMR, 13C NMR, and IR spectroscopies. A DFT B3LYP/6-311G(d,p) study of the reaction's arenium-cation mechanism of (E)-1 and (Z)-1 giving 2 and 3, respectively, indicated the reaction's regioselectivity and kinetic control. The analogous reaction of 1-(1′-naphthoyl)pyrene gave exclusively 13H-benz[4,5]indeno[2,1-a]pyren-13-one. Contrary to previous claims, the preferred formation of five-member rings in Scholl reactions is not unexpected.
AB - Intramolecular Scholl reaction of 1-benzoylpyrene (1) gave 8H-dibenzo[def,qr]chrysen-8-one (2) and 11H-indeno[2,1-a]pyren-11-one (3) in a 1:2 ratio. The structures of 2 and 3 were determined, using 1H NMR, 13C NMR, and IR spectroscopies. A DFT B3LYP/6-311G(d,p) study of the reaction's arenium-cation mechanism of (E)-1 and (Z)-1 giving 2 and 3, respectively, indicated the reaction's regioselectivity and kinetic control. The analogous reaction of 1-(1′-naphthoyl)pyrene gave exclusively 13H-benz[4,5]indeno[2,1-a]pyren-13-one. Contrary to previous claims, the preferred formation of five-member rings in Scholl reactions is not unexpected.
UR - http://www.scopus.com/inward/record.url?scp=84996557792&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.6b01798
DO - 10.1021/acs.joc.6b01798
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AN - SCOPUS:84996557792
SN - 0022-3263
VL - 81
SP - 11389
EP - 11393
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 22
ER -