Fluorosulfonyl azide
Chemical compound
From Wikipedia, the free encyclopedia
Fluorosulfonyl azide is an inorganic compound with the chemical formula FN3O2S. This is a derivative of sulfuric acid containing a fluorine atom and an azide group. The compound is used as a reagent for transferring diazo groups.[1]
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| Names | |
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| Preferred IUPAC name
N-Diazosulfamoyl fluoride | |
| Identifiers | |
3D model (JSmol) |
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PubChem CID |
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| Properties | |
| FN3O2S | |
| Molar mass | 125.08 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis
Fluorosulfonyl azide can be prepared by reacting disulfuryl fluoride (F2S2O5) with sodium azide in nitromethane or sulfolane.[2]
Chemical properties
Fluorosulfonyl azide is a diazo group transfer reagent.[3] It is suitable, for example, for preparing azides from primary amines in a click reaction.[4] Diazo reagents can be prepared starting from dimethyl 2-oxopropylphosphonate using fluorosulfonyl azide. If diazabicycloundecene is added as a base, the Ohira-Bestmann reagent is obtained. With magnesium oxide, the Seyferth-Gilbert reagent dimethyldiazomethylphosphonate is obtained.[5]
These reagents are used to convert aldehydes into alkynes. With the two precursors, such a reaction is also possible as a one-pot synthesis. In this case, an aldehyde is added directly and potassium carbonate is used as the base.[5]