Fluorosulfonyl azide

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Fluorosulfonyl azide is an inorganic compound with the formula FN3O2S. It contains a fluorine atom and an azide group and is mainly used as a reagent to transfer diazo groups in chemical reactions. Its Preferred IUPAC name is N-diazosulfamoyl fluoride.

Synthesis
Fluorosulfonyl azide can be made by reacting disulfuryl fluoride (F2S2O5) with sodium azide in nitromethane or in sulfolane.

Chemical properties and uses
- It is a diazo group transfer reagent, useful for moving diazo groups from one molecule to another.
- One common application is converting primary amines into azides, which is valuable in click chemistry.
- Fluorosulfonyl azide can also be used to prepare other diazo-transfer reagents from simple starting materials. For example:
- Starting from dimethyl 2-oxopropylphosphonate, fluorosulfonyl azide can lead to the Ohira–Bestmann reagent if diazabicycloundecene is used as the base.
- Using magnesium oxide yields the Seyferth–Gilbert reagent.
- These diazo-transfer reagents are used to transform aldehydes into alkynes. In a one-pot process, an aldehyde can be combined with a base such as potassium carbonate and fluorosulfonyl azide to form the corresponding alkyne.

See also
- Diphenylphosphoryl azide
- Sulfuryl diazide
- Trifluoromethanesulfonyl azide
- Tosyl azide