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SO2F2-Promoted Dehydration of Aldoximes: A Rapid and Simple Access to Nitriles

Yiyong Zhao, Guangyao Mei, Haibo Wang, Guofu Zhang*, Chengrong Ding*

*College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China, Email:,

Y. Zhao, G. Mei, H. Wang, G. Zhang, C. Ding, Synlett, 2019, 30, 1484-1488.

DOI: 10.1055/s-0037-1611840

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The use of SO2F2 as a reagent enables a rapid, simple and mild dehydration of aldoximes to give the corresponding nitriles. A variety of (hetero)arene, alkene, alkyne and aliphatic aldoximes can be converted to nitriles in excellent yields with great functional group compatibilities in acetonitrile under ambient conditions. An eco-friendly protocol with aqueous methanol as solvent is also described.

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Care is required in performing chemistry in which SO2F2 is employed. Although SO2F2 is a colorless, odorless gas that is not immediately irritating to the eyes or skin, it is a broad-spectrum biocide at high concentrations or prolonged exposures and should only be handled with adequate ventilation. Furthermore, repeated exposure to high levels of sulfuryl fluoride may cause lung and kidney damage.

Key Words

SO2F2, aldoximes, nitriles, dehydration, CH3CN, aqueous methanol

ID: J72-Y2019