Reactions between 5-Nitroso-1,3-diphenyltetrazolium Salts and Electron-Rich Arenes, Amines, Thiophenol, Sulfoxides, and Thioanisole

A series of reactions between 5-nitroso-1,3-diphenyltetrazolium tetrafluoroborate and methoxybenzenes, amines, thiols, sulfoxides, and sulfides, most of which are generally accepted as being inert to nitroso groups, is reported here. The tetrazolium-activated nitroso functionality is capable of oxidizing the aforementioned substrates to give the corresponding oxidized products, and the nitroso tetrazolium itself is transformed into the corresponding amide or hydroxyamide, depending on the nature of the reaction partners. In the case of thioanisole, an addition product was obtained.