Abstract
When 2, 3, 5, 6-tetrachlorobenzenediazonium hydrogen sulfate in acetic acid-sulfuric acid was decomposed in sulfuric acid at 150-160°C, 2, 3, 5, 6-tetrachlorophenylacetic acid and 1, 2, 4, 5-tetrachlorobenzene were obtained together with a large amount of resinous materials. On the other hand, 2, 3, 5, 6-tetrachlorobenzenediazonium salt was found to be converted into 3, 4, 6-trichlorobenzene-2-diazo-1-oxide at low temperatures (70-80°C) in acetic acid-sulfuric acid. The results obtained in the presence of a radical scavenger, ferric chloride, indicated that 2, 3, 5, 6-tetrachlorophenylacetic acid was produced via 2, 3, 5, 6-tetrachlorophenyl radical formed by homolytic decomposition of the diazonium salt at high temperatures (150-160°C), whereas a heterolytic reaction to form 2, 3, 5, 6-tetrachlorophenol scarcely occurred. The above mentioned diazo-oxide, which, might be formed even at high temperatures, actually decomposed at the melting point (117-118°C) to produce resinous materials.
