A Diels–Alder super diene breaking benzene into C2H2 and C4H4 units

Yusuke Inagaki, Masaaki Nakamoto and Akira Sekiguchi ()
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Yusuke Inagaki: Graduate School of Pure and Applied Sciences, University of Tsukuba
Masaaki Nakamoto: Graduate School of Pure and Applied Sciences, University of Tsukuba
Akira Sekiguchi: Graduate School of Pure and Applied Sciences, University of Tsukuba

Nature Communications, 2014, vol. 5, issue 1, 1-6

Abstract: Abstract Cyclic polyene with six carbon atoms (benzene) is very stable, whereas cyclic polyene with four carbon atoms (cyclobutadiene) is extremely unstable. The electron-withdrawing pentafluorophenyl group of a substituted cyclobutadiene lowers the energy of the lowest unoccupied molecular orbital, greatly increasing its reactivity as a diene in Diels–Alder reactions with acetylene, ethylene and even benzene. Here we show that the reaction with benzene occurs cleanly at the relatively low temperature of 120 °C and results in the formal fragmentation of benzene into C2H2 and C4H4 units, via a unique Diels–Alder/retro-Diels–Alder reaction. This is a new example of the rare case where breaking the C–C bond of benzene is possible with no activation by a transition metal.

Date: 2014
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Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:5:y:2014:i:1:d:10.1038_ncomms4018

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DOI: 10.1038/ncomms4018

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