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Trifluoromethanesulfonyl azide

Trifluoromethanesulfonyl azide or triflyl azide is an organic azide used as a reagent in organic synthesis.

Preparation

Trifluoromethanesulfonyl azide is prepared by treating trifluoromethanesulfonic anhydride with sodium azide, traditionally in dichloromethane. However, the use of dichloromethane is avoided since it can generate highly explosive azido-chloromethane and diazidomethane. The reaction may also instead be conducted in toluene, acetonitrile, or pyridine.

(Tf = )

An alternative route starts from imidazole-1-sulfonyl azide.

Reactions

Trifluoromethanesulfonyl azide generally converts amines to azides.

See also

References