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31.23.2.1.3 Method 3: Diazotization and Oxidation of Aminoarenes in Acidic Media

DOI: 10.1055/sos-SD-031-01557

O'Leary, P.Science of Synthesis, (2007311394.

Oxidation of an aminoarene may occur; thus, when 3,5-dinitroaniline is treated with nitric acid and sulfuric acid, an oxygen atom is inserted at C2 to give the unstable inner salt 108 (Scheme 43).[‌135‌] Although the scope of this method is limited, a similar reaction of 2,3,5-trichloroaniline also leads to a 2-diazoniophenolate; however, an intermediate compound that forms during this synthesis is explosive.[‌136‌]

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