A Concise, Catalyst-Free Synthesis of Davis’ Oxaziridines using Sodium Hypochlorite
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. Optimi...
| Main Authors: | , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Georg Thieme Verlag KG
2019-01-01
|
| Series: | SynOpen |
| Subjects: | |
| Online Access: | http://www.thieme-connect.de/DOI/DOI?10.1055/s-0037-1611722 |
| _version_ | 1828776855121952768 |
|---|---|
| author | Saori Kitagawa Hiromitsu Mori Tatsuya Odagiri Katsuya Suzuki You Kikkawa Rie Osugi Shinobu Takizawa Yoshikazu Kimura Masayuki Kirihara |
| author_facet | Saori Kitagawa Hiromitsu Mori Tatsuya Odagiri Katsuya Suzuki You Kikkawa Rie Osugi Shinobu Takizawa Yoshikazu Kimura Masayuki Kirihara |
| author_sort | Saori Kitagawa |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-11T16:09:30Z |
| format | Article |
| id | doaj.art-f83371b7f18641b0818387fc83e84173 |
| institution | Directory Open Access Journal |
| issn | 2509-9396 |
| language | English |
| last_indexed | 2024-12-11T16:09:30Z |
| publishDate | 2019-01-01 |
| publisher | Georg Thieme Verlag KG |
| record_format | Article |
| series | SynOpen |
| spelling | doaj.art-f83371b7f18641b0818387fc83e841732022-12-22T00:59:07ZengGeorg Thieme Verlag KGSynOpen2509-93962019-01-010301212510.1055/s-0037-1611722A Concise, Catalyst-Free Synthesis of Davis’ Oxaziridines using Sodium HypochloriteSaori Kitagawa0Hiromitsu Mori1Tatsuya Odagiri2Katsuya Suzuki3You Kikkawa4Rie Osugi5Shinobu Takizawa6Yoshikazu Kimura7Masayuki Kirihara8Department of Materials and Life ScienceDepartment of Materials and Life ScienceR&D Department of ChemicalsDepartment of Materials and Life ScienceDepartment of Materials and Life ScienceDepartment of Materials and Life ScienceThe Institute of Scientific and Industrial Research (ISIR)Research and Development DepartmentDepartment of Materials and Life ScienceAbstract 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.http://www.thieme-connect.de/DOI/DOI?10.1055/s-0037-1611722oxaziridinedavis’ oxaziridinesodium hypochloritesodium hypochlorite pentahydrate n-sulfonylimineoxidation |
| spellingShingle | Saori Kitagawa Hiromitsu Mori Tatsuya Odagiri Katsuya Suzuki You Kikkawa Rie Osugi Shinobu Takizawa Yoshikazu Kimura Masayuki Kirihara A Concise, Catalyst-Free Synthesis of Davis’ Oxaziridines using Sodium Hypochlorite SynOpen oxaziridine davis’ oxaziridine sodium hypochlorite sodium hypochlorite pentahydrate n-sulfonylimine oxidation |
| title | A Concise, Catalyst-Free Synthesis of Davis’ Oxaziridines using Sodium Hypochlorite |
| title_full | A Concise, Catalyst-Free Synthesis of Davis’ Oxaziridines using Sodium Hypochlorite |
| title_fullStr | A Concise, Catalyst-Free Synthesis of Davis’ Oxaziridines using Sodium Hypochlorite |
| title_full_unstemmed | A Concise, Catalyst-Free Synthesis of Davis’ Oxaziridines using Sodium Hypochlorite |
| title_short | A Concise, Catalyst-Free Synthesis of Davis’ Oxaziridines using Sodium Hypochlorite |
| title_sort | concise catalyst free synthesis of davis oxaziridines using sodium hypochlorite |
| topic | oxaziridine davis’ oxaziridine sodium hypochlorite sodium hypochlorite pentahydrate n-sulfonylimine oxidation |
| url | http://www.thieme-connect.de/DOI/DOI?10.1055/s-0037-1611722 |
| work_keys_str_mv | AT saorikitagawa aconcisecatalystfreesynthesisofdavisoxaziridinesusingsodiumhypochlorite AT hiromitsumori aconcisecatalystfreesynthesisofdavisoxaziridinesusingsodiumhypochlorite AT tatsuyaodagiri aconcisecatalystfreesynthesisofdavisoxaziridinesusingsodiumhypochlorite AT katsuyasuzuki aconcisecatalystfreesynthesisofdavisoxaziridinesusingsodiumhypochlorite AT youkikkawa aconcisecatalystfreesynthesisofdavisoxaziridinesusingsodiumhypochlorite AT rieosugi aconcisecatalystfreesynthesisofdavisoxaziridinesusingsodiumhypochlorite AT shinobutakizawa aconcisecatalystfreesynthesisofdavisoxaziridinesusingsodiumhypochlorite AT yoshikazukimura aconcisecatalystfreesynthesisofdavisoxaziridinesusingsodiumhypochlorite AT masayukikirihara aconcisecatalystfreesynthesisofdavisoxaziridinesusingsodiumhypochlorite AT saorikitagawa concisecatalystfreesynthesisofdavisoxaziridinesusingsodiumhypochlorite AT hiromitsumori concisecatalystfreesynthesisofdavisoxaziridinesusingsodiumhypochlorite AT tatsuyaodagiri concisecatalystfreesynthesisofdavisoxaziridinesusingsodiumhypochlorite AT katsuyasuzuki concisecatalystfreesynthesisofdavisoxaziridinesusingsodiumhypochlorite AT youkikkawa concisecatalystfreesynthesisofdavisoxaziridinesusingsodiumhypochlorite AT rieosugi concisecatalystfreesynthesisofdavisoxaziridinesusingsodiumhypochlorite AT shinobutakizawa concisecatalystfreesynthesisofdavisoxaziridinesusingsodiumhypochlorite AT yoshikazukimura concisecatalystfreesynthesisofdavisoxaziridinesusingsodiumhypochlorite AT masayukikirihara concisecatalystfreesynthesisofdavisoxaziridinesusingsodiumhypochlorite |