The formation of the unexpected bicyclic compound 16 via the pyrolytic isomerisation of 4-nonafluorobiphenyl prop-2-enyl ether 8 can be rationalised by invoking the intermediacy of a rare retro-cyclisation reaction of the internal Diels–Alder adduct 12 (from the Claisen intermediate 9) to a tethered ketene 18, recyclisation via the alternative mode to 17 and its subsequent transformation.
A. S. Batsanov, G. M. Brooke, D. Holling and A. M. Kenwright, Chem. Commun., 1999, 1549 DOI: 10.1039/A903209F
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