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Bis(2-methoxyethyl)aminosulfur Trifluoride: A New Broad-Spectrum Deoxofluorinating Agent with Enhanced Thermal Stability
Abstract
Bis(2-methoxyethyl)aminosulfur trifluoride, (CH 3 OCH 2 CH 2 ) 2 NSF 3 (Deoxo-Fluor reagent), is a new deoxofluorinating agent that is much more thermally stable than DAST (C 2 H 5 ) 2 NSF 3 and its congeners. It is effective for the conversion of alcohols to alkyl fluorides, aldehydes/ketones to the corresponding gem -difluorides, and carboxylic acids to the trifluoromethyl derivatives with, in some cases, superior performance compared to DAST. The enhanced stability is rationalized on the basis of conformational rigidity imposed by a coordination of the alkoxy groups with the electron-deficient sulfur atom of the trifluoride.
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Cites
Lee, C., Yang, W., & Parr, R. G. (1988) · Physical Review B · doi:10.1103/physrevb.37.785 · Cited by 100,874
Organofluorine Chemistry: Principles and Commercial Applications
(1994) · doi:10.1007/978-1-4899-1202-2 · Cited by 1,691
Cited by
Monofluorination of Organic Compounds: 10 Years of Innovation
Champagne, P. A., Desroches, J., Hamel, J.-D., Vandamme, M., & Paquin, J.-F. (2015) · Chemical Reviews · doi:10.1021/cr500706a · Cited by 963
Xia, J.-B., Zhu, C., & Chen, C. (2013) · Journal of the American Chemical Society · doi:10.1021/ja410815u · Cited by 560
Late-stage difluoromethylation: concepts, developments and perspective
Sap, J. B. I., Meyer, C. F., Straathof, N. J. W., Iwumene, N., am Ende, C. W., Trabanco, A. A., & Gouverneur, V. (2021) · Chemical Society Reviews · doi:10.1039/d1cs00360g · Cited by 432
Metadata
- Authors
- Lal, G. S., Pez, G. P., Pesaresi, R. J., Prozonic, F. M., & Cheng, H.
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1999-08-21
- Volume
- 64
- Issue
- 19
- Pages
- 7048-7054
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W2179395831
- Cited by
- 407
- References
- 2
- FWCI
- 5.49
- Type
- journal article
- Language
- en
- Open access
- closed
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- Lal, G. S., Pez, G. P., Pesaresi, R. J., Prozonic, F. M., & Cheng, H. (1999). Bis(2-methoxyethyl)aminosulfur Trifluoride: A New Broad-Spectrum Deoxofluorinating Agent with Enhanced Thermal Stability. The Journal of Organic Chemistry. https://doi.org/10.1021/jo990566%2B
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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