Structural effects controlling the rate of the retro-Diels-Alder reaction in anthracene cycloadducts

9,10‐Diaminoanthracenes Revisited: The Influence of N‐Substituents on Their Electronic States

“…Molecular and electronics tructures in the neutral state Syntheses of 1 [6] and 3 [4] have been reported previously,a nd Nanisyl-N-methyl-substituted 9,10-diaminoanthracene 2 was newly obtained from 9,10-dibromoanthracenea nd N-methyl-4methoxyanilineb yaBuchwald-Hartwig amination reaction, [7,8] similart ot he approach for obtaining 3.F rom the X-ray crystallographic determination, the two dianisylaminog roups of 3 were seen to adopta ne clipsedc onformation,a nd the torsional angle of the dianisylamino group with respectt ot he 9,10anthrylene moiety was between about 728 and7 4 8,i ng ood agreement with the B3LYP/6-31G** results. [4] Such al arge torsional angle indicates steric congestion between the 9,10-anthrylenem oiety and the substituted amino groups.…”

Diels–Alder reactions of anthracene, 9-substituted anthracenes and 9,10-disubstituted anthracenes

“…123 In another study, the thermal cycloaddition reaction of a 9,10-disubstituted anthracene derivative was used to investigate the possibility of inter-bead reactions of polystyrene resin beads. 124 The reactions of beads with bound 9,10-disubstituted anthracene and beads with bound maleimide were carried out in toluene and DMF.…”

Fluorination of Bi- and polycyclic aromatic hydrocarbons with N-fluorobis(phenylsulfonyl)amine in the absence of solvent

“…The ratio of compounds XVII and XVIII weakly depended on the temperature variation. This ratio is sometimes higher than at the application of N-fl uoro-2,4-dinitroimidazole in CH 2 Cl 2 [35] or of N-fluoropyridinium triflate in ClCH 2 CH 2 Cl [36]. At the use of the reagent F-TEDA-BF 4 in CF 3 COOH the fl uorination products did not form at all, and the main product was 9-trifl uoroacetoxyanthracene [27].…”