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Recently azides have been identified as a new precursor of primary nitroalkanes by oxidation. In this context, Rozen et al. [26] found that the carbon-bonded nitrogen of azides would be nucleophilic enough to interact with the oxygen atom of HOF·CH₃CN. Thus, thanks to the efficiency of this oxidant, a variety of azides, easily obtainable from alkyl bromides and sodium azide, have been converted into primary nitroalkanes in quantitative or very good yields and in short reaction times (Scheme 1.15).

Scheme 1.15 Oxidation of azides using HOF·CH₃CN.

Concerning the use of fluorine, a very corrosive material, it should be used only with the appropriate vacuum line techniques. However, for the occasional user, various premixed mixtures of F₂ in inert gases are commercially available.

Moreover, as for the oxidation of primary amines, a flow process has been developed [19] and, following this procedure, quantitative yields (<90%) of primary and secondary nitroalkanes were obtained.