Organic Letters
Organic Letters
5 years ago

Skeletal Rearrangement of Twisted Polycyclic Aromatic Hydrocarbons under Scholl Reaction Conditions

Skeletal Rearrangement of Twisted Polycyclic Aromatic Hydrocarbons under Scholl Reaction Conditions
Yoshito Tobe, Shunpei Nobusue, Kazuya Fujita
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01341

DOI: 10.1021/acs.orglett.7b01341

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