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Synthesis 2016; 48(15): 2361-2375
DOI: 10.1055/s-0035-1561454
DOI: 10.1055/s-0035-1561454
short review
The Chemistry of Unusually Functionalized Azides
Further Information
Publication History
Received: 11 April 2016
Accepted: 18 April 2016
Publication Date:
07 June 2016 (online)
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
-
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For other quantum chemical calculations to characterize ethynyl azides, see:
For reviews, see:
Transformations similar to the reaction 35 → 32w:
For examples, see: