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Synlett 2009(14): 2217-2235  
DOI: 10.1055/s-0029-1217553
ACCOUNT
© Georg Thieme Verlag Stuttgart ˙ New York

Diazenes as Powerful and Versatile Tools in Organic Synthesis

Janez Košmrlj, Marijan Kočevar, Slovenko Polanc*
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, 1000 Ljubljana, Slovenia
Fax: +386(1)2419271; e-Mail: slovenko.polanc@fkkt.uni-lj.si;
Further Information

Publication History

Received 23 December 2008
Publication Date:
15 July 2009 (online)

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Abstract

This account describes the application of diazenes as electrophiles in reactions with alkenes, arenes, aldehydes, ketones, and some other compounds, as well as a variety of transformations that take advantage of the oxidative properties of diazenes.

1 Introduction

2 Synthesis of Diazenes

3 Allylic Amination

4 Electrophilic Amination of Aromatic Substrates

4.1 Application of Diazenedicarboxylates

4.2 Aminations Involving Carbamoyldiazenecarboxylates

5 Reactions of Diazenes with Carbonyl Compounds

5.1 Aminations with Diazenedicarboxylates

5.2 Transformations Employing Carbamoyldiazenecarboxylates

6 Diazenecarboxamides as Precursors for Azoles and Related Reactions

6.1 Condensed 1,2,4-Triazoles

6.2 1,3,4-Oxadiazoles

6.3 1,2,4-Triazoles

7 Selective Oxidation of Thiols To Give Disulfides: Chemical and Biochemical Implications

7.1 Oxidation of Thiols and Selenols

7.2 Electrochemistry

7.3 Biochemical Properties of Diazenecarboxamides

8 Other Applications of Diazenes

9 Conclusions

Key words

diazenes - electrophilic aminations - selective oxidations - complexes - biological activity

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21

Košmrlj, J.; Kočevar, M.; Polanc, S. unpublished results.