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A one-pot method for the synthesis of 3-(hetero-)aryl-1,4,2-dioxazol-5-ones

Authors :
Jason D. Masuda
Alexander W. H. Speed
Toren Hynes
J. R. Dahn
David S. Hall
Source :
Canadian Journal of Chemistry. 98:158-163
Publication Year :
2020
Publisher :
Canadian Science Publishing, 2020.

Abstract

3-R-1,4,2-dioxazol-5-ones are a class of compounds that are increasingly finding diverse uses, including as regioselective amidation reagents and as electrolyte additives that enable long cycling lifetimes in rechargeable lithium-ion batteries. Conventional methods for their synthesis tend to be slow and time-consuming, requiring isolation and thorough drying of a hydroxamic acid intermediate, followed by a separate cyclization step with N,N′-carbonyldiimidazole. Furthermore, the cyclization is typically performed in dichloromethane, an environmentally harmful solvent. This work demonstrates a new one-pot method for the synthesis of these compounds that eliminates the need for isolation of the intermediate or the use of halogenated solvents. The reaction is mainly performed using environmentally benign ethyl acetate and a relatively small amount of N,N-dimethylformamide. The reaction proceeds readily at room temperature and requires no expensive metal catalysts to function.

Details

ISSN :
14803291 and 00084042
Volume :
98
Database :
OpenAIRE
Journal :
Canadian Journal of Chemistry
Accession number :
edsair.doi...........4464ef0689f7ff9cea6c6dc6892cbc8b
Full Text :
https://doi.org/10.1139/cjc-2019-0419