Regioselectivity in the Controversial Scholl Reaction of 1-Benzoylpyrene: Formation of a Five-Member Ring Is Not Unexpected

Yaacov Netanel Oded, Sergey Pogodin, Israel Agranat*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

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, 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.

Original languageEnglish
Pages (from-to)11389-11393
Number of pages5
JournalJournal of Organic Chemistry
Volume81
Issue number22
DOIs
StatePublished - 18 Nov 2016

Bibliographical note

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© 2016 American Chemical Society.

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