Aryl azides from triazenes

The synthesis and mechanism of formation of a triazene from an arenediazonium ion and an amine with one or two aliphatic substituents (see Scheme 13-1, R = alkyl, R = H or alkyl) will be discussed in Section 13.2. Here we will briefly mention Dimroth s method (1903, 1905 a) for synthesis of wholly aliphatic triazenes (Scheme 13-6, R and R = alkyl). Dimroth obtained these by the action of Grignard reagents on alkyl azides followed by isolation via copper(i) salts. The Grignard method can also be applied for the synthesis of triazenes with an aromatic substituent by using an aryl azide. 

For example, the triazene (228) is obtained from ditizotized anthra-quinone and ammonium carbonate under these conditions " (equation 115). Further, the formation of aryl azides by oxidation of aryl triazenes with hypochlorite solution has been reported In a related... 

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