Nucleophilic aromatic substitution with dialkoxycarbenes

Article abstract of DOI:10.1139/v97-159

Dimethoxycarbene, generated at 110°C by thermolysis of 2,2-dimethoxy-5,5-dimethyl-Δ³-1,3,4-oxadiazoline, displaces fluoride from aromatic rings that are activated with electron-withdrawing groups. Intermolecular substitution on Sanger's reagent and on hexafluorobenzene are reported, together with intramolecular substitution by a dioxycarbene with a tethered aryl group.