Selective Reactions on the Azido Groups of Aromatic Polyazides

Aromatic azides are widely used as starting materials in organic synthesis and as photoaffinity labeling reagents in molecular biology. When aromatic azides have two or more nonequivalent azido groups, these groups can selectively react with dipolarophiles, nucleophiles, and reductants or undergo selective thermolysis and photolysis. Such selective reactions open up principally new ways for the directed synthesis of organic compounds and the use of aromatic azides as photoaffinity labeling reagents. This account is devoted to all types of selective reactions on nonequivalent azido groups of aromatic azides which were recently discovered and studied in our group. 1 Introduction 2 Selective 1,3-Dipolar Cycloadditions 3 Selective Staudinger Reactions 4 Selective Reduction 5 Selective Nucleophilic Replacements 6 Selective Thermolysis 7 Selective Photolysis and gamma-Radiolysis 8 Products of the Selective Reactions in Photochemical Studies 9 Conclusions and Prospects