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Synlett 2009(1): 1-8  
DOI: 10.1055/s-0028-1087479
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© Georg Thieme Verlag Stuttgart ˙ New York

Selective Reactions on the Azido Groups of Aromatic Polyazides

Sergei V. Chapyshev
Institute of Problems of Chemical Physics, Russian Academy of Sciences, 142432 Chernogolovka, Moscow Region, Russian Federation
Fax: +7(496)5249676; e-Mail: chap@icp.ac.ru;
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Publication History

Received 6 May 2008
Publication Date:
12 December 2008 (online)

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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

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