Di- and polyazides. Synthesis, chemical transformations and practical applications

The chemistry of organic di- and polyazides has been extensively developed in recent years. Methods for the synthesis of 1,1- and 1,2-diazides are diverse and include stoichiometric, catalytic, photochemical and electrochemical approaches. These organic compounds are highly reactive and are involved in a wide range of reactions, from thermal transformations to click chemistry. Of particular attention are transformations, in which one azido group undergoes intramolecular cyclization, while another azido group remains intact and can participate in further chemical transformations. Tri- and polyazides are investigated as precursors for the production of high-energy materials and the synthesis of high-molecular-weight compounds. This review addresses the methods for the synthesis of organic compounds containing two or more azido groups and their chemical transformations. Aliphatic, aromatic and heteroaromatic diazides are considered. Specific transformations characteristic of geminal and vicinal diazides, which differ from the reactions of monoazides, are described. Examples of the practical application of di-, tri- and polyazides are highlighted.The bibliography includes 355 references