Abstract
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 γ-Radiolysis
8 Products of the Selective Reactions in Photochemical Studies
9 Conclusions and Prospects
Key words
azides - regioselectivity - selective cycloadditions - selective Staudinger reactions
- selective
reductions
