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Unexpected α,α′-difluoroethers from Ag(i)F and N-bromosuccinimide reactions of dibenzo[a,e]cyclooctatetraene

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Abstract

An unexpected and highly efficient reaction of dibenzo[a,e]cyclooctatetraene with Ag(I)F and N-bromosuccinamide in dichloromethane results in a sequential ring contraction pathway to generate bridged bicyclic α,α′-difluoroether isomers 10 and 11 where the ether oxygen is isotopically labelled from oxygen-18 water. In diethyl ether the same reaction generates the more classical vicinal difluoride isomers 13 and 14.

Graphical abstract: Unexpected α,α′-difluoroethers from Ag(i)F and N-bromosuccinimide reactions of dibenzo[a,e]cyclooctatetraene

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Publication details

The article was received on 19 Aug 2019, accepted on 05 Nov 2019 and first published on 05 Nov 2019


Article type: Communication
DOI: 10.1039/C9CC06426E
Chem. Commun., 2019, Advance Article

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    Unexpected α,α′-difluoroethers from Ag(I)F and N-bromosuccinimide reactions of dibenzo[a,e]cyclooctatetraene

    Z. Fang, R. Z. Gillatt, A. M. Z. Slawin, D. B. Cordes, C. L. Carpenter-Warren and D. O'Hagan, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9CC06426E

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