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CC BY-ND-NC 4.0 · SynOpen 2019; 03(01): 21-25
DOI: 10.1055/s-0037-1611722
DOI: 10.1055/s-0037-1611722
paper
A Concise, Catalyst-Free Synthesis of Davis’ Oxaziridines using Sodium Hypochlorite
This work was performed under the Cooperative Research Program of the ‘Network Joint Research Center for Materials and Devices’.Weitere Informationen
Publikationsverlauf
Received: 15. Dezember 2018
Accepted after revision: 23. Januar 2019
Publikationsdatum:
19. Februar 2019 (online)
Abstract
N-Sulfonyloxaziridines (Davis’ oxaziridines) can be synthesized by reacting the corresponding N-sulfonylimines with aqueous sodium hypochlorite in acetonitrile without any catalyst. The pH of the aqueous sodium hypochlorite is crucial to obtain the product in high yield. Optimized conditions are presented that allow synthetically useful Davis’ oxaziridines to be easily obtained in up to 90% yields from the corresponding imines by using inexpensive, stable, environmentally friendly sodium hypochlorite pentahydrate crystals as the oxidant, with high reproducibility.