Arene oxides with azides

A stereospecific synthesis of aziridine 266 has been reported by Ittah et al. from arene oxide 1 by treatment with sodium azide, followed by tri-phenylphosphine reaction. The reaction proceeds via a phosphonium hydroxide intermediate (267).157... 

Azides are utilized for various C-C cleavage reactions [45]. For example, the alkylarene 78 v ras converted to the aniline 81 upon treatment with n-nonyl azide and an iron catalyst under oxidative reaction conditions (Scheme 7.30). Oxidation of the arene 78 generates the benzyhc cation 79, which reacts with the azide. Subsequent Schmidt rearrangement generates the iminium cation 80, which hydrolyzes to form the aniline 81. This method was applicable to degradation of low molecular weight polystyrenes to arylamines [45c]. 

Yao B, Liu Y, Zhao L, Wang DX, Wang MX (2014) Designing a Cu(ll)-ArCu(ll)-ArCu (lll)-Cu(l) catalytic cycle Cu(ll)-catalyzed oxidative arene C-H bond azidation with air as an oxidant under ambient conditions. J Org Chem 79(22) 11139-11145... 

Sulfoxides are oxidized to sulfoximides by HN3 in the presence of H2SO4 [1, 19]. The nucleophilic substitution of chloride by azide is accelerated, when the solution of HN3 and alkyl halide is allowed to react in a column filled with acidic AI2O3 [20]. The exchange of halide substituents of arenes by azide requires activating groups in other positions of the aromatic system. Pyridine derivatives frequently yield tetrazoles [8]. Aromatic C-nitroso compounds and twice the molar quantity of HN3 form the aromatic azide, N2, and H2O... 

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