Schmelzreaktionen mit Aluminiumchlorid. 6. Mitteilung [1]. Zur kenntnis der carbazolierung von anthrimiden in aluminiumchlorid‐schmelzen

Abstract

Summary. The behaviour of di-(1-anthraquinony1)-aminc, when cyclised in pyridine-aluminium chloride or pure aluminium chloride fusions, has bcen comparcd. The formation of blue educt complexes with aluminium chloride in the latter case has been revealed as a factor which inhibits cyclisation. The results are discussed and generaliscd, classifying carbazolation of anthrimides as an intramolecular SchoZZ-type reaction.In der letzten Mitteilung L l ] haben wir iiber die Carbazolierung von Di-(1-anthrachinony1)-amin (1)

Comparison of Oxidative Aromatic Coupling and the Scholl Reaction

“…This new direction sparked methodological developments. In 1971, Wick revealed that the cyclization of di‐(1‐anthraquinonyl)amine into 1,2;7,8‐diphthaloylcarbazole (C. I. Vat Yellow 28) proceeds more efficiently in the presence of an AlCl 3 /pyridine complex than in an AlCl 3 /NaCl melt 20. Other variants include the use of AlCl 3 in high‐boiling solvents such as dichlorobenzene and trichlorobenzene,21 low‐melting complex AlCl 3 /SO 2 ,22 or of ZrCl 4 23.…”

Scholl reaction as a powerful tool for the synthesis of nanographenes: a systematic review

“…He reported that the former complex system is superior to the latter (Scheme 8). 37 This new process also triggered the synthetic developments of aromatic hydrocarbon extension. In 1990, Zavada and co-workers developed a method for the cross coupling of 2-naphthols 20a and 20b using an oxidant to selectively construct C-C bonds in binaphthyls such as 21.…”

“…He reported that the former complex system is superior to the latter ( Scheme 8 ). 37 This new process also triggered the synthetic developments of aromatic hydrocarbon extension.…”

Oxidative aromatische Kupplung und Scholl‐Reaktion im Vergleich

“…1971 zeigte Wick, dass die Cyclisierung von Di‐(1‐anthrachinoyl)amin zu 1,2;7,8‐Diphthaloylcarbazol (“C. I. Vat Yellow 28”) in Gegenwart eines AlCl 3 ‐Pyridin‐Komplexes effizienter verläuft als in einer AlCl 3 ‐NaCl‐Schmelze 20. In anderen Varianten werden AlCl 3 in hochsiedenden Lösungsmitteln wie Dichlorbenzol und Trichlorbenzol,21 der niedrig schmelzende Komplexes AlCl 3 ‐SO 2 22 oder ZrCl 4 eingesetzt 23.…”