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Geminal Diazides Derived from 1,3-Dicarbonyls: A Protocol for Synthesis
Hellmuth Erhardt1, Andreas P Häring1, Andreas Kotthaus1
1Organic Chemistry, Bergische Universität Wuppertal , Gaußstraße 20, 42119 Wuppertal, Germany.
The Journal of Organic Chemistry
|December 2, 2015
Summary
Synthesizing rare geminal diazides is now accessible. This study introduces a new method using 1,3-dicarbonyl compounds, molecular iodine, and sodium azide for general geminal diazide synthesis.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Geminal diazides are a rare class of organic compounds.
- Existing synthetic methods for geminal diazides are limited.
Purpose of the Study:
- To develop a general and accessible method for synthesizing geminal diazides.
- To explore the scope and limitations of the new synthetic approach.
Main Methods:
- Reaction of 1,3-dicarbonyl compounds (malonates, 3-oxoesters, 1,3-diketones) with molecular iodine and sodium azide.
- Utilizing aqueous dimethyl sulfoxide (DMSO) as a solvent system.
- Characterization of synthesized geminal diazides and assessment of their thermal stability.
Main Results:
- A broad range of geminal diazides with diverse structural motifs were synthesized.
- The method demonstrated selectivity, enabling diazidation even in the presence of competing 1,3-dicarbonyls.
- Several synthesized diazides were evaluated for their thermal stability.
Conclusions:
- The presented method offers a general access to geminal diazides from readily available 1,3-dicarbonyl precursors.
- The reaction is efficient and tolerates various functional groups and sterically demanding substituents.
- The study expands the synthetic toolbox for accessing this rare class of compounds.