Insertion reaction of azidosulfonyl azo dye with model alicyclic and heterocyclic compounds

Thermal reactions of 4-(2-hydroxynaphthalen-1-yldiazenyl)benzenesulfonyl azide with cyclohexane, benzene, toluene, anisole, p -xylene, mesitylene, dihydropyran, and pyridine were studied. Structures of the resulting azo dyes were confirmed by FT-IR, UV, 1 H and 13 C NMR, and mass spectra and elemental analyses, and their solvatochromic properties were examined. Probable mechanisms of nitrene insertion were discussed.