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Regioselectivity in the Controversial Scholl Reaction of 1-Benzoylpyrene: Formation of a Five-Member Ring Is Not Unexpected

“…4 mp 242 °C), IR ν = 1697 cm −1 (CO). 6 Preda and Scott reported that 2 (mp 214−216 °C) was formed by FVP of 1-(2-bromobenzoyl)pyrene at 1100 °C, also referring to Vollmann's mp of 242 °C for 2. 7 Both reports provided 1 H NMR spectra of their products.…”

“…7 Both reports provided 1 H NMR spectra of their products. 6,7 Clar also referred to the alleged Scholl reaction product 2, 8 whereas 3 was only briefly mentioned as an environmental sample. 9 Balaban and Nenitzescu reformulated the Scholl reaction as "the elimination of two aryl-bound hydrogens accompanied by the formation of an aryl−aryl bond under the influence of a Friedel−Crafts catalyst".…”

Why 6-Methylpentacene Deconjugates but Avoids the Thermally Allowed Unimolecular Mechanism

“…Dihydro derivatives of various polycyclic aromatic hydrocarbons (PAH) have been found to undergo different types of hydrogen-transfer reactions . A general stepwise nonchain radical mechanism was established to explain various hydrogenation and dehydrogenation reactions. 10a,b Hydrogen transfer was also found to be involved in the formation of graphitic species and other disproportionation byproducts from PAHs 10c-e likely involved in defect formation in pentacene thin films 10e.…”

Doublet Open‐Shell Graphene Fragments

“…[46] The melting behaviors of 5 was studied by Lewis and Kovac in 1978 by differential scanning calorimetry and hotstage microscopy, [47] and Morgenthaler and Rüchardt recorded the ESR spectra of methylated 3 and pristine 4 as intermediates in hydrogen transfer reactions in 1999. [48] The most recent study of 5 was reported by Fox et al in 2015, taking advantage of the cutting-edge scanning tunnelling microscopy and non-contact atomic force microscopy techniques to generate and visualize 5 on the surface. [49] A few theoretical studies on 5 were also worth mentioning, including the study on the charge effects that strengthened the π-stacking pancake bonding for pristine and fluorinated 5 by Cui and Kertesz et al [50] and the reaction and adsorption behaviors of 5 on metal surfaces.…”

“…Later in 1972, Nowakowski managed to assign the proton hyperfine splitting constants with the aid of McLachlan's method [46] . The melting behaviors of 5 was studied by Lewis and Kovac in 1978 by differential scanning calorimetry and hot‐stage microscopy, [47] and Morgenthaler and Rüchardt recorded the ESR spectra of methylated 3 and pristine 4 as intermediates in hydrogen transfer reactions in 1999 [48] . The most recent study of 5 was reported by Fox et al .…”