Abstract
Reactions ofO-phenyldibenzofuranium tetrafluoroborate with nucleophiles (OH−, NO2 −, AcO−) in aqueous media follow the SNAr-mechanism and involve dehydroarenes. In DMSO, this salt smoothly reacts with NO2 − and I− with predominant opening of the furan ring. 10-Phenylxanthonium tetrafluoroborate readily arylates the NO2 − 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 Bayer—Villiger oxidation of this salt affords xanthone and 2-phenoxybenzoic acid.
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