Synthesis of 1,3-Diaryltriazenes and Azo Dyes from Aryl Amines Using N-Nitrososulfonamides

Abstract

AbstractNew methods for the synthesis of 1,3-diaryltriazenes and azo dyes from aryl amines are reported. Both methods involve the formation of aryl diazonium intermediates via the transnitrosation of aryl amines with N-nitrososulfonamides. Each two-step transformation may be performed in one reaction vessel at room temperature with no precautions taken to exclude air or moisture. Several triazene and azo dye structures are reported here for the first time, demonstrating the utility of operating the two-step reaction sequence under mild conditions.