Английская Википедия:Acyl azide

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Файл:Acyl azide.svg
General chemical structure of an acyl azide

Acyl azides are carboxylic acid derivatives with the general formula RCON3. These compounds, which are a subclass of organic azides, are generally colorless.[1]

Preparation

Typically acyl azides are generated under conditions where they rearrange to the isocyanate.[1]

Alkyl or aryl acyl chlorides react with sodium azide to give acyl azides.[2][3]

Файл:Preparation of acyl azides from acyl chlorides.png

The second major route to azides is from the acyl hydrazides with nitrous acid.[1]

Acyl azides have also been synthesized from various carboxylic acids and sodium azide in presence of triphenylphosphine and trichloroacetonitrile catalysts in excellent yields at mild conditions.[4] Another route starts with aliphatic and aromatic aldehydes reacting with iodine azide which is formed from sodium azide and iodine monochloride in acetonitrile.[5]

Uses

On Curtius rearrangement, acyl azides yield isocyanates.[6][7]

Файл:Curtius Rearrangement Scheme.png

Acyl azides are also formed in Darapsky degradation,[8][9][10]

Darapsky degradation

Historical references

References

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