Thermolysis of biphenylene toward cyclo-ortho-phenylenes

The solvent and catalyst free thermolysis of biphenylenes at 350 °C furnishes [n]cyclo-ortho-phenylenes ([n]COPs, n=4-10) in one step and in high yields. At 400 °C biphenylene dimerizes into tetraphenylene, but lower reaction temperatures produce cyclooligomers. If suitably substituted, the oligomer...

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Hauptverfasser: Ehjeij, Daniel (VerfasserIn) , Rominger, Frank (VerfasserIn) , Bunz, Uwe H. F. (VerfasserIn) , Freudenberg, Jan (VerfasserIn) , Müllen, Klaus (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: February 19, 2024
In: Angewandte Chemie. International edition
Year: 2024, Jahrgang: 63, Heft: 8, Pages: 1-6
ISSN:1521-3773
DOI:10.1002/anie.202312040
Online-Zugang:Verlag, kostenfrei, Volltext: https://doi.org/10.1002/anie.202312040
Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.202312040
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Verfasserangaben:Daniel Ehjeij, Frank Rominger, Uwe H.F. Bunz, Jan Freudenberg, and Klaus Müllen

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520 |a The solvent and catalyst free thermolysis of biphenylenes at 350 °C furnishes [n]cyclo-ortho-phenylenes ([n]COPs, n=4-10) in one step and in high yields. At 400 °C biphenylene dimerizes into tetraphenylene, but lower reaction temperatures produce cyclooligomers. If suitably substituted, the oligomers are soluble and can be isolated and characterized. The products are exclusively cyclic. In the crystalline state, [6]COP displays an alternating crown-shaped conformation. 
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