Reactions of O-phenyldibenzofuranium tetrafluoroborate with nucleophiles (OH-, NO?-, AcO-) in aqueous media follow the SzsAr-mechanism and involve dehydroarenes. In DMSO, this salt smoothly reacts with NO,-and I-with predominant opening of the furan ring. 10-Phenylxanthonium tetrafluoroborate readily arytates the NO,-ion in water (at the N and O atoms), mainly with predominant opening of the central ring, and is completely decomposed even with weak bases (NH2OH, 2,4-dinitrophenylhydrazine). The Baeyer--Villiger oxidation of this salt affords xanthone and 2-phenoxybenzoic acid.