DOI: 10.1039/A903209F
(Paper)
Reference Section for: Chem. Commun., 1999, 1549-1550
Pyrolysis reactions of 4-nonafluorobiphenyl prop-2-enyl ether: a remarkable rearrangement reaction
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Andrei S. Batsanov, Gerald M. Brooke, Darren Holling and Alan M. Kenwright
Abstract
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.
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