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The reaction of sodium azide with perfluorobenzene, containing an electron-withdrawing group, under microwave irradiation results in the fast preparation of p-substituted tetrafluorophenyl monoazides. Having an excess of sodium azide and a strong electron-withdrawing group like NO2 or CN, fluorophenyl diazides are also produced upon conventional or microwave heating. A synergic effect between the amount of sodium azide and the electron-withdrawing character of the substituents is observed giving different products. A discussion on the products and reaction mechanism is presented.

Microwave-assisted pyrolysis of o-nitrophenyl azides gives benzofuroxans in good yields in short reaction times.

The reaction produces good yields only with crystalline o-nitrophenylazides (melting points above 50 °C).

The conversion of substrates (I) into 2-azido derivatives is followed by spontaneous N2 elimination to form the target compounds.