Ring expansion of 11H-benzo[b]fluorene-11-methanols and related compounds leading to 17,18-diphenyldibenzo[a,o]PENTAPHENE (cas 222-93-5) and related polycyclic aromatic hydrocarbons with extended conjugation and novel architectures
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Add time:09/28/2019 Source:infona.pl
Condensation between 7-(1,1-dimethylethyl)-13-phenyl-8H-indeno[2,1-b]phenanthrene and paraformaldehyde produced the corresponding 9-fluorenylmethanol derivative, which on treatment with P 2 O 5 to promote a Wagner–Meerwein rearrangement for ring expansion furnished 14-phenyldibenzo[a,j]anthracene in 88% yield. Similarly, 17,18-diphenyldibenzo[a,o]pentaphene possessing a helical twist and bearing two phenyl substituents at the most sterically congested C17 and C18 positions and other related compounds were likewise synthesized. Subsequent intramolecular arylation reactions involving the phenyl substituents produced polycyclic aromatic hydrocarbons with novel architectures.
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