I. Synthesis and Reactivity of Geodesic Polyarenes and Heterocycles. II. Intramolecular Reactions and Rearrangements of Gas-phase Aryl Radicals
Chapters 5 and 6 describe mechanistic studies aimed at understanding the behavior of aryl radicals in the gas-phase under FVP conditions. Specifically, translocations of hydrogen atoms in a 1,5-manner across a cove region are demonstrated to be viable processes. In addition, larger phenyl and naphthyl substituents are shown to be capable of migrating around the perimeter of PAH radicals by means of 1,2-aryl shifts. Supporting evidence for these rearrangements is provided by isolation of cyclized products resulting from strategically placed radical traps in the aromatic molecules.
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13C NMR 1H of major acid Anhydrous aromatic aryl aryl radicals azabowl bay regions benzene bond bromine calcd calculations carbon nanotube CDCI3 Chem chemical shift chloride color change concentrated to dryness cooled to room corannulene crude product crude pyrolysate cyclodehydrogenation desired product dibenzo[a,g]corannulene dichloromethane Diels-Alder addition dienophile dimer dried over magnesium dryness under vacuum eluent endcap Figure flash vacuum pyrolysis flask geodesic polyarene H NMR hexanes HRMS DART-TOF HRMS ESI+ hydrocarbon hydrogen i i i i imide intramolecular arylation isolated magnesium sulfate major diastereomer MALDI-TOF methanol mixture of diastereomers mixture was cooled mixture was stirred mmol molecule nitrogen NMR 125 MHz NMR 500 MHz NMR spectrum pad of silica perylene reaction mixture reactivity rearomatization room temperature round-bottom flask Scott short pad shown in Scheme silica gel solution solvent starting material synthesis UV-vis X=Br yellow solid