Aromatic azides aniline formation

DUTT - WORMALL Azide formation Synthesis of aromatic azides from anilines via diazonium salts. 

The reaction of benzene with sodium azide in the presence of concentrated sulfuric acid or aluminum chloride catalyst was first explored by Schmidt, giving aniline in low yield (Eq. 2.8) [96]. Later, Kovacic investigated the mechanism of Lewis Acids catalyzed aromatic amination with hydrazoic acid [97]. Aminodiazonium ion could also be used for the direct amination of aromatics. Olah and coworkers investigated the protonation of hydrazoic acid and alkyl azides with superacid, such as FSOsH/SbFs, HF/SbFs, or HF/BF3, finding the formation of stable aminodia-zomium ions by H, NMR spectroscopic studies [98]. The aminodiazo-... 

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