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Journal Article
Research Support, Non-U.S. Gov't
Skeletal Rearrangement of Twisted Polycyclic Aromatic Hydrocarbons under Scholl Reaction Conditions.
Organic Letters 2017 June 17
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.
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