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

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

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

2019

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.

显示更多 [+]