Journal
ORGANIC LETTERS
Volume 2, Issue 10, Pages 1489-1492Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol005849z
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[GRAPHICS] Flash vacuum pyrolysis of benzo[b]biphenylene, an alternant polycyclic aromatic hydrocarbon (PAH), gives fluoranthene, a nonalternant PAH, as the major product at 1100 degrees C in the gas phase. The most reasonable mechanism to explain this isomerization involves equilibrating diradicals of 5-phenylnaphthalene that rearrange by the net migration of a phenyl group to give equilibrating diradicals of 1 phenylnaphthalene, one isomer of which then cyclizes to fluoranthene.
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