Facile Method for the Synthesis of Vicinal Azidoiodides by the Reaction of the NaN3-I-2 System with Unsaturated Compounds

A facile and efficient method was developed for the synthesis of vicinal azidoiodides in 62-77% yields by the reaction of sodium azide and iodine with unsaturated compounds in methanol, aqueous methanol, or the water-methanol-tetrahydrofuran solvent system. The reaction in Et2O or CHCl3 produced only vicinal diiodides.