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Communication | Special issue | Vol 103, No. 2, 2021, pp.699-706
Published online, 23rd March, 2021
DOI: 10.3987/COM-20-S(K)68
Chloroamidation of Alkenes Using Sodium Hypochlorite Pentahydrate and Its Application to Synthesis of Aziridines

Masayuki Kirihara,* Kouta Adachi, Yugo Sakamoto, Kazuki Tujimoto, Sho Yamahara, Ryoji Matsushima, Yukou Namba, Kosuke Sato, Takashi Kamada, Yoshikazu Kimura, and Shinobu Takizawa*

*The Institute of Scientific and Industrial Research, Osaka University, 8-1, Mihogaoka, Ibaraki, Osaka 567-0047, Japan

Abstract

The reaction of alkenes with sodium hypochlorite pentahydrate (NaOCl·5H2O) and phosphoric acid (H3PO4) in nitrile solvents resulted in a chloroamidation reaction, producing -chloroamide derivatives in good yields without the use of a transition metal catalyst (up to 90%). N-Pivalazirizines were readily obtained from the resulting -chloroamide derivatives when they were reacted with lithium hexamethyldisilazide (LiHMDS).