Which way to go: The product distribution in the efficient oxidation of 2‐aminoanthracene derivatives to pyrazine‐ and pyrrole‐fused bisanthracenes can be controlled by additives (see scheme; TFA=trifluoroacetic acid, DDQ=2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone). The pyrrole‐fused dimer can be regarded as an aza[7]helicene with a stable helical conformation.
Which way to go: The product distribution in the efficient oxidation of 2‐aminoanthracene derivatives to pyrazine‐ and pyrrole‐fused bisanthracenes can be controlled by additives (see scheme; TFA=trifluoroacetic acid, DDQ=2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone). The pyrrole‐fused dimer can be regarded as an aza[7]helicene with a stable helical conformation.
In the 19th century F. F. Runge synthesized a black material through the oxidation of aniline. This substance was named “aniline black” by W. H. Perkin, and is now a well‐known black dye. In their Communication on H. Shinokubo et al. discuss a novel aspect of this reaction of aromatic amines, namely the selective formation of diazaacenes and azahelicenes from aminoanthracene derivatives. The product distribution can be effectively controlled by the reaction conditions.
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