The Chemistry of Unusually Functionalized Azides

Abstract

This short review describes the synthesis and reactions of organic azides bearing an adjacent additional functional group, such as azidoacetylenes, α-azido alcohols, geminal azidohalo compounds, formyl azide, 1,1-diazidoethenes, and azidocyclopentadienes. Some of these compounds were extensively investigated in previous quantum chemical studies, but experimental access was missing until quite recently; other such azides were simply overlooked for a long time. The title compounds are able to undergo a variety of intramolecular and intermolecular subsequent reactions, which can find application in synthetic chemistry. 1 Introduction 2 Ethynyl Azides 3 Geminal Azidohalo Compounds and α-Azido Alcohols 3.1 Azidohalomethanes 3.2 Discovery and Synthesis of α-Azido Alcohols 3.3 Reactions of α-Azido Alcohols 4 Formyl Azide 5 1,1-Diazidoethenes 6 Azidocyclopentadienes 7 Conclusion and Outlook.