Issue 95, 2019

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

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

Supplementary files

Article information

Article type
Communication
Submitted
19 Aug 2019
Accepted
05 Nov 2019
First published
05 Nov 2019

Chem. Commun., 2019,55, 14295-14298

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, 55, 14295 DOI: 10.1039/C9CC06426E

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