Skeletal Rearrangement of Twisted Polycyclic Aromatic Hydrocarbons under Scholl Reaction Conditions

Shunpei Nobusue, Kazuya Fujita, Tobe Yoshito*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

22 Scopus citations

Abstract

Treatment of a twisted polycyclic aromatic hydrocarbon containing cyclooctatetraene fused by two 9,9′-bifluorenylidene units under the Scholl reaction conditions (FeCl3 or 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and scandium trifluoromethanesulfonate) led to stepwise skeletal rearrangements to afford initially a hydrocarbon with a seven-membered ring and then tetrabenzo[a,d,j,m]coronene with all six-membered rings. The course of the rearrangement was interpreted in terms of the acid-catalyzed isomerization of 9,9′-bifluorenylidene into dibenzo[g,p]chrysene moieties on the basis of theoretical investigations.

Original languageEnglish
Pages (from-to)3227-3230
Number of pages4
JournalOrganic Letters
Volume19
Issue number12
DOIs
StatePublished - 16 Jun 2017

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