An efficient, inexpensive, and shelf-stable diazotransfer reagent: imidazole-1-sulfonyl azide hydrochloride.
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. Crucially, this reagent can be prepared in a one-pot reaction on a large scale from inexpensive materials, is shelf-stable, and is conveniently crystalline.
Goddard-Borger
Ethan D
ED
Chemistry M313, School of Biomedical, Biomolecular & Chemical Sciences, The University of Western Australia, Crawley WA 6009, Australia. goddae01@student.uea.edu.au
Stick
Robert V
RV
D001386:Azides / Q000138:chemical synthesis* / Q000737:chemistry / Q000191:economics; D002152:Calorimetry, Differential Scanning; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D001386:Azides; D007093:Imidazoles; C523862:imidazole-1-sulfonyl azide hydrochloride