Phenyl migrations in dehydroaromatic compounds. A new mechanistic link between alternant and nonalternant hydrocarbons at high temperatures
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 2-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.
Preda
DV
Boston College, Merkert Chemistry Center, Chestnut Hill, Massachusetts, 02467-3860, USA.
Scott
LT