Reactions with Geminal Diazides: Long Known, Full of Surprises, and New Opportunities

Abstract

Geminal diazides are uncommon yet powerful tools in organic synthesis. The chemistry of this class of functional compounds is characterized by quite unusual reactivities, including fragmentations and degradations, along with known reactions of organic azides. This Short Review highlights the major reactivities of various structural units having geminal diazido moieties, and provides an overview on the synthetic opportunities of such compounds.

1 Introduction

2 Preparation of Geminal Diazides

3 Reactivities of Geminal Diazides

3.1 α,α-Diazido Carbonyls

3.2 1,3-Diketones

3.3 Diazidated β-Ketoesters

3.4 Diazidated Malonates

3.5 Diazidated Malonamides

3.6 Miscellaneous Geminal Diazides

4 Conclusion

Key words

geminal diazides - azidation - heterocycles - fragmentation - acylation

Publication History

Received: 31 May 2022

Accepted after revision: 28 June 2022

Article published online:
18 August 2022

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