2003
DOI: 10.1002/ange.200301667
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Neuere Entwicklungen in der Synthese Helicen‐artiger Moleküle

Abstract: [4] führten zur Herstellung von racemischen Helicenbis(chinonen), wobei eine Diels-Alder-Reaktion verwendet wurde (Schema 1), [5] die um eine effiziente Methode für die erforderliche Racematspaltung ergänzt wurde.[6] Trotz bemerkenswerter Fortschritte in der Helicenchemie bleibt die Entwicklung neuer, kurzer, effizienter und atomökonomi- [7]Helicen durch "Carbenoid-Kupplung". dppp = 1,3-Bis(diphenylphosphanyl)propan, NBS = N-Bromsuccinimid, LiHMDS = Lithiumhexamethyldisilazid, HMPA = Hexamethylphosphoramid.

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Cited by 138 publications
(34 citation statements)
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“…In summary, we have developed a novel synthesis of substituted [5] helicenes from the readily modifiable 1,1'-binaphthyls. For example, substituted [6]helicenes could be formed from mixed oxidative couplings between 3-phenanthrol and various 2-naphthols.…”
mentioning
confidence: 99%
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“…In summary, we have developed a novel synthesis of substituted [5] helicenes from the readily modifiable 1,1'-binaphthyls. For example, substituted [6]helicenes could be formed from mixed oxidative couplings between 3-phenanthrol and various 2-naphthols.…”
mentioning
confidence: 99%
“…[5] The need for more highly substituted and structurally varied helicenes has led to the development of new methods as replacements of the classical synthesis by the photocyclization of stilbenes.…”
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confidence: 99%
“…[10] The challenge of developing efficient routes to helicenes that are amenable to scale-up has inspired many imaginative approaches, [11,12] including strategies based on Diels-Alder cycloadditions, [13] carbenoid insertions, [14] radical cyclizations, and metal-mediated cycloisomerizations. [15,16] Herein, we report a short and efficient entry to helicenes, azahelicenes, and phenanthrenes in which the use of halo and alkoxy substituents to control both the stereochemical course of Wittig reactions and the regiochemical course of homolytic aromatic substitution reactions is a key feature.…”
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confidence: 99%
“…[16] Such aesthetically pleasing structures are also associated with cross-conjugated p systems for carbon-carbon frameworks, however, in the b-oligothiophenes all sulfur atoms are positioned at the molecular periphery, thereby facilitating multiple short Scheme 1. Synthesis of octabutylcyclo [8]thiophene 6.…”
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confidence: 99%
“…The only limit is imagination. Very recently, the first chiral Möbius [16]annulene hydrocarbons were described, which has opened a debate about their aromaticity. [20] It is probably the moment to introduce some sulfur (thiophenes) in the Möbius annulenes area to discover new organic electronic materials.…”
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confidence: 99%