Dedicated to Professor Heinrich Lang on the occasion of his 60th birthday
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
Key words
azides - cycloaddition - hazardous compounds - low-temperature NMR spectroscopy -
photolysis - reactive intermediates - trapping reactions
