Von Triarylmethyl-Kationen zu ausgedehnten para-chinoiden p-Systemen und gespannten Ringverbindungen
p-systems can easily be formed by a new preparative method. Similar to the SNAr-reaction sterically shielded triarylmethyl-cations react with different C-and N-nucleophiles to dipolar para-quinonedimethanes. The use of coordinating endgroups allows the synthesis of twice-substituted products, which show solvatochromism and halochromism. Intramolecular neighbouring group effects are introduced by 1,8-donor- acceptor-substituited naphthalene derivatives. Especially the Me2N-substituent interacts with a peri-located triarylmethyl-cation under cyclization. The reaction of (8-Chloro-1-naphtyl)-bis(4-methoxy-phenyl)-methyl- tetrafluoroborate with malonitrile leads to 1-Dicyano-2-bis-(4-methoxyphenyl)- acenaphthene as another model compound for stretched ring systems
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