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Preparation of 5-Substituted 1 H-Tetrazoles from Nitriles in Water
Abstract
The addition of sodium azide to nitriles to give 1H-tetrazoles is shown to proceed readily in water with zinc salts as catalysts. The scope of the reaction is quite broad; a variety of aromatic nitriles, activated and unactivated alkyl nitriles, substituted vinyl nitriles, thiocyanates, and cyanamides have all been shown to be viable substrates for this reaction.
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Cited by
Marrying click chemistry with polymerization: expanding the scope of polymeric materials
Golas, P. L., & Matyjaszewski, K. (2010) · Chem. Soc. Rev. · doi:10.1039/b901978m · Cited by 863
Ligand design for functional metal–organic frameworks
Almeida Paz, F. A., Klinowski, J., Vilela, S. M. F., Tomé, J. P. C., Cavaleiro, J. A. S., & Rocha, J. (2012) · Chem. Soc. Rev. · doi:10.1039/c1cs15055c · Cited by 855
Noodleman, L., Lovell, T., Han, W.-G., Li, J., & Himo, F. (2004) · Chemical Reviews · doi:10.1021/cr020625a · Cited by 373
An overview of injectable polymeric hydrogels for tissue engineering
Sivashanmugam, A., Arun Kumar, R., Vishnu Priya, M., Nair, S. V., & Jayakumar, R. (2015) · European Polymer Journal · doi:10.1016/j.eurpolymj.2015.05.014 · Cited by 366
Why Is Tetrazole Formation by Addition of Azide to Organic Nitriles Catalyzed by Zinc(II) Salts?
Himo, F., Demko, Z. P., Noodleman, L., & Sharpless, K. B. (2003) · Journal of the American Chemical Society · doi:10.1021/ja030204q · Cited by 353
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Metadata
- Authors
- Demko, Z. P., & Sharpless, K. B.
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2001-11-01
- Volume
- 66
- Issue
- 24
- Pages
- 7945-7950
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W1969872919
- Cited by
- 971
- References
- 0
- FWCI
- 11.50
- Type
- journal article
- Language
- en
- Open access
- closed
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- Demko, Z. P., & Sharpless, K. B. (2001). Preparation of 5-Substituted 1 H-Tetrazoles from Nitriles in Water. The Journal of Organic Chemistry. https://doi.org/10.1021/jo010635w
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