title: Regioselectivity in the Controversial Scholl Reaction of 1-Benzoylpyrene: Formation of a Five-Member Ring Is Not Unexpected.
abstract: 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, using1H 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.
authors: Organic Chemistry, Institute of Chemistry, The Hebrew University of Jerusalem , Philadelphia Building #212, Edmond J. Safra Campus, Jerusalem 9190401, Israel.
authors: Yaacov Netanel
authors: YN
authors: Oded
authors: Organic Chemistry, Institute of Chemistry, The Hebrew University of Jerusalem , Philadelphia Building #212, Edmond J. Safra Campus, Jerusalem 9190401, Israel.
authors: Sergey
authors: S
authors: Pogodin
authors: Organic Chemistry, Institute of Chemistry, The Hebrew University of Jerusalem , Philadelphia Building #212, Edmond J. Safra Campus, Jerusalem 9190401, Israel.
authors: Israel
authors: I
authors: Agranat