Preparation of Large Perphenylbiaryls: Can Intermolecular Coupling Compete with Intramolecular Cyclization of Precursors?
Abstract: The highly substituted naphthalenes 1,2,3,4,5,6,7‐heptaphenylnaphthalene (13), 2,3,4,5,6,7,8‐heptaphenyl‐1‐naphthol (12), 1‐bromo‐2,3,4,5,6,7,8‐heptaphenylnaphthalene (4), and 1‐(phenylethynyl)‐2,3,4,5,6,7,8‐heptaphenylnaphthalene (5) were prepared by a variety of methods, and all but 5 were crystallographically characterized. The attempted Ullmann coupling of 4 to give tetradecaphenyl‐1,1′‐binaphthyl (3), at both 270 °C and 350 °C, yielded instead 1,2,3,4,5,6‐hexaphenylfluoranthene (17) via an intramolecular cyclization reaction. When the alkyne 5 was heated with tetracyclone (6) at 350 °C, 1‐(pentaphenylphenyl)‐2,3,4,5,6,7,8‐heptaphenylnaphthalene (7) was formed in 3 % yield. However, greater amounts of 5,6,7,8,9,14‐hexaphenyldibenzo[a,e]pyrene (20, 11 %) and 1,2,3,4,5,6,7‐heptaphenylfluoranthene (21, 11 %) were produced, the former by intramolecular cyclization and dehydrogenation of 5 and the latter by an intramolecular Diels‐Alder reaction of 5 followed by extrusion of acetylene. The X‐ray structure of 7 shows it to be an exceptionally crowded biaryl, and the X‐ray structure of 20 shows it to be a saddle shaped polycyclic aromatic hydrocarbon.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Preparation of Large Perphenylbiaryls: Can Intermolecular Coupling Compete with Intramolecular Cyclization of Precursors? ; day:06 ; month:11 ; year:2024 ; extent:13
Chemistry - a European journal ; (06.11.2024) (gesamt 13)
- Creator
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Finch, Ki F.
Zhang, Xiaodong
McSkimming, Alex
Pascal, Robert A.
- DOI
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10.1002/chem.202402897
- URN
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urn:nbn:de:101:1-2411081330476.082264702416
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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15.08.2025, 7:23 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Finch, Ki F.
- Zhang, Xiaodong
- McSkimming, Alex
- Pascal, Robert A.
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