Abstract
Crystalline 2-ethylimidazole-1-sulfonyl azide was designed as a convenient reagent with improved thermal stability for electrophilic azidation of carbanions. The compound crystallized in the monoclinic space group P21/c. The molecules are arranged into chains by short C–H...O contacts along a two-fold screw axis. The quaternary 1-azidosulfonyl-2-ethyl-3-methylimidazolium tetrafluoroborate crystallized in Fdd2 with two independent ion pairs which engage in C–H...F interactions.
Highlights
Azides are versatile building blocks which play an important role in synthetic chemistry [1,2]
The capacity of an imidazole-1-sulfinate as an excellent leaving group resembles that of a benzenesulfinate
We planned to address the following issues: a) the solid hydrochloride is clearly not suitable for use with lithiated species, a free base is desired b) imidazole-1-sulfonyl azide is liquid, but a solid is preferred for improved handling c) the acidic 2-position of the imidazole should be blocked to facilitate its use with strong bases d) solubility of the reagent in aprotic solvents is requested
Summary
Azides are versatile building blocks which play an important role in synthetic chemistry [1,2]. They can be used in “click chemistry” [3,4,5,6] to introduce heterocyclic structures and serve as a latent amino group [7]. Imidazole-1-sulfonyl azide hydrochloride was introduced as a new efficient and inexpensive diazo-transfer reagent [16]. Diazo-transfer reagents can act as reagents for electrophilic azidation of carbanions [17,18,19,20,21]. 2-ethylimidazole-1-sulfonyl azide which we designed to offer several advantages over existing reagents regarding solubility and stability
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