CC BY-ND-NC 4.0 · SynOpen 2019; 03(01): 21-25
DOI: 10.1055/s-0037-1611722
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A Concise, Catalyst-Free Synthesis of Davis’ Oxaziridines using Sodium Hypochlorite

Saori Kitagawa
a   Department of Materials and Life Science, Shizuoka Institute of Science and Technology, 2200-2 Toyosawa, Fukuroi, Shizuoka 437-8555, Japan   eMail: kirihara.masayuki@sist.ac.jp
,
Hiromitsu Mori
a   Department of Materials and Life Science, Shizuoka Institute of Science and Technology, 2200-2 Toyosawa, Fukuroi, Shizuoka 437-8555, Japan   eMail: kirihara.masayuki@sist.ac.jp
,
Tatsuya Odagiri
b   R&D Department of Chemicals, Nippon Light Metal Company, Ltd., Kambara, Shimizu-ku, Shizuoka 421-3203, Japan
,
Katsuya Suzuki
a   Department of Materials and Life Science, Shizuoka Institute of Science and Technology, 2200-2 Toyosawa, Fukuroi, Shizuoka 437-8555, Japan   eMail: kirihara.masayuki@sist.ac.jp
,
You Kikkawa
a   Department of Materials and Life Science, Shizuoka Institute of Science and Technology, 2200-2 Toyosawa, Fukuroi, Shizuoka 437-8555, Japan   eMail: kirihara.masayuki@sist.ac.jp
,
Rie Osugi
a   Department of Materials and Life Science, Shizuoka Institute of Science and Technology, 2200-2 Toyosawa, Fukuroi, Shizuoka 437-8555, Japan   eMail: kirihara.masayuki@sist.ac.jp
,
c   The Institute of Scientific and Industrial Research (ISIR), Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047, Japan
,
d   Research and Development Department, Iharanikkei Chemical Industry Co. Ltd., Kambara, Shimizu-ku, Shizuoka 421-3203, Japan
,
a   Department of Materials and Life Science, Shizuoka Institute of Science and Technology, 2200-2 Toyosawa, Fukuroi, Shizuoka 437-8555, Japan   eMail: kirihara.masayuki@sist.ac.jp
› Institutsangaben
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.

 
  • References and Notes


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