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

Zeguo Fang, Roscoe Z. Gillatt, Alexandra M. Z. Slawin, David B. Cordes, Cameron L. Carpenter-Warren, David O'Hagan*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

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.

Original languageEnglish
Pages (from-to)14295-14298
Number of pages4
JournalChemical Communications
Volume55
Issue number95
Early online date5 Nov 2019
DOIs
Publication statusPublished - 11 Dec 2019

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