Desulfurization of Thioamides into Amides with Dinitrogen Tetroxide

Article abstract of DOI:10.1055/s-1986-31844

Secondary and tertiary thioamides or diphenylthionocarbonate reacted readily with dinitrogen tetroxide at ca. 0 deg C in acetonitrile to afford the corresponding amides or carbonate in good to excellent yields.The desulfurization appears to proceed via an S-nitroso intermediate by the selective electrophilic attack of nitrosonium cation on the thione sulfur atom.