Utility of a Polymeric Azide Reagent in the Formation of Di- and Triazidomethane. Their NMR Spectra and the X-ray Structure of Derived Triazoles

The use of a polymeric azidation reagent for the preparation of explosive azidomethanes at ambient temperature is described. Thus, methyl iodide was converted into methyl azide, methylene bromide and methylene chloride into diazido methane, and bromoform into triazido methane. ¹H and ¹³C NMR spectra, including ¹J_CH, of the azidomethanes are described. The X-ray diffraction of derived triazole adducts 4 and 5 confirms the structure assignment and indicates in the case of 5 a 1,5-sigmatropic alkyl rearrangement.