Crystal Structure of 2-Ethylimidazole-1-sulfonyl Azide: A New Azidation Reagent
Abstract
:1. Introduction
2. Results and Discussion
2.1. Design and Synthesis
- 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
2.2. Crystal Structures of 1 and 2
Interaction | H...F | C...F | C–H...F | Symmetry code (F) |
C3–H...F | 2.399(8) | 3.14(1) | 135.3(6) | x, –1/2 + y, –1/2 + z |
C4–H...F | 2.56(2) | 3.44(2) | 148.9(6) | –1/4 + x,–1/4 – y,–3/4 + z |
C5–H...F | 2.57(2) | 3.26(2) | 128.3(8) | –1/4 + x,–1/4 – y,–3/4 + z |
C6–H...F | 2.29(1) | 3.19(1) | 155.3(7) | 1/4 – x,–1/4 + y,–1/4 + z |
C9–H...F | 2.47(2) | 3.29(2) | 146.0(7) | – |
C10–H...F | 2.404(8) | 3.14(1) | 131.3(6) | 1/4 – x,–1/4 + y,3/4 + z |
C11–H...F | 2.57(1) | 3.22(2) | 124.3(7) | 1/4 – x,–1/4 + y,–1/4 + z |
2.3. Reactivity and Stability
3. Experimental Section
3.1. Synthesis of 2-Ethylimidazole-1-sulfonyl Azide (1)
3.2. Synthesis of 1-Azidosulfonyl-3-alkyl-2-ethylimidazolium Tetrafluoroborates (2 and 3)
3.3. Synthesis of 1-Azidosulfonyl-3-alkyl-2-ethylimidazolium Triflimides (2a and 3a)
3.4. Azidation of 4-Methoxybiphenyl
3.5. X-ray Data Collection and Structure Refinement
4. Conclusions
Acknowledgments
References and Notes
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Laus, G.; Adamer, V.; Hummel, M.; Kahlenberg, V.; Wurst, K.; Nerdinger, S.; Schottenberger, H. Crystal Structure of 2-Ethylimidazole-1-sulfonyl Azide: A New Azidation Reagent. Crystals 2012, 2, 118-126. https://doi.org/10.3390/cryst2010118
Laus G, Adamer V, Hummel M, Kahlenberg V, Wurst K, Nerdinger S, Schottenberger H. Crystal Structure of 2-Ethylimidazole-1-sulfonyl Azide: A New Azidation Reagent. Crystals. 2012; 2(1):118-126. https://doi.org/10.3390/cryst2010118
Chicago/Turabian StyleLaus, Gerhard, Verena Adamer, Michael Hummel, Volker Kahlenberg, Klaus Wurst, Sven Nerdinger, and Herwig Schottenberger. 2012. "Crystal Structure of 2-Ethylimidazole-1-sulfonyl Azide: A New Azidation Reagent" Crystals 2, no. 1: 118-126. https://doi.org/10.3390/cryst2010118
APA StyleLaus, G., Adamer, V., Hummel, M., Kahlenberg, V., Wurst, K., Nerdinger, S., & Schottenberger, H. (2012). Crystal Structure of 2-Ethylimidazole-1-sulfonyl Azide: A New Azidation Reagent. Crystals, 2(1), 118-126. https://doi.org/10.3390/cryst2010118