Imidazole-1-sulfonyl azide is an organic azide compound that can be used as an alternative organic synthesis reagent to trifluoromethanesulfonyl azide. It is an explosive colorless liquid, but some of its organic-soluble salts can be safely handled and stored as a solid.

Aug 22, 2007 · The design and synthesis of a new diazotransfer reagent, imidazole-1-sulfonyl azide hydrochloride, are reported. This reagent has proven to equal triflyl azide in its ability to act as a “diazo donor” in the conversion of both primary amines into azides and activated methylene substrates into diazo compounds.

Trifluoromethanesulfonyl azide is prepared by treating trifluoromethanesulfonic anhydride with sodium azide, traditionally in dichloromethane. [1] However, the use of dichloromethane is avoided since it can generate highly explosive azido-chloromethane and diazidomethane.

In situ preparation of sulfonyl chlorides from thiols by oxidation with N-chlorosuccinimide (NCS), tetrabutylammonium chloride, and water followed by reaction with amine or sodium azide in the same reaction vessel enables a convenient synthesis of sulfonamides and sulfonyl azides.

Triflyl azide serves as an efficient diazo transfer reagent in a direct synthesis of sulfonyl azide building blocks from readily available and stable sulfonamides. The process is experimentally simple, mild, and high-yielding.

Several diazo transfer reagents are analyzed using the same DSC protocol and found to have higher thermal stability, which is in general agreement with the reported values. For sulfonyl azide reagents, an average ΔH D of −201 kJ mol –1 is observed.

Mar 21, 2016 · Imidazole-1-sulfonyl azide and salts thereof are valuable reagents for diazo-transfer reactions, most particularly conversion of primary amines to azides. The parent reagent and its HCl salt present stability and detonation risks, but …

Jul 11, 2011 · Whereas alkyl and aryl azides readily react with terminal alkynes to afford 1,4-disubstituted-1,2,3-triazoles in excellent yields and selectivity in the presence of a copper catalyst, sulfonyl, phosphoryl, and certain acyl azides allow additional chemistry upon ring-opening of the corresponding copper–triazole intermediates.

May 6, 2014 · Imidazole-1-sulfonyl azide hydrogen sulfate is presented as an efficient reagent for the synthesis of sulfonyl azides from primary sulfonamides. The described method is experimentally simple and high-yielding and does not require the addition of Cu salts.

Jun 6, 2014 · Imidazole-1-sulfonyl azide hydrogen sulfate is presented as an efficient reagent for the synthesis of sulfonyl azides from primary sulfonamides. The described method is experimentally simple and high-yielding and does not require the addition of Cu salts.