Aromatic substitution. Part XIX. Arylation of aromatic compounds with benzenediazonium tetrafluoroborate in homogeneous solution

Abstract

The decomposition of benzenediazonium tetrafluoroborate in solution in an aromatic solvent and either acetonitrile or sulpholan has been studied quantitatively. The isomer ratios and total rate ratios for the phenylations of the aromatic substrates confirm that the reactive intermediate is probably a diradical cation (II). Two possible mechanisms for these substitutions are discussed.