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An Isolable and Bench-Stable Epoxidizing Reagent Based on Triazine: Triazox

Kohei Yamada , Yuki Igarashi, Tatsuki Betsuyaku, Masanori Kitamura, Koki Hirata, Kazuhito Hioki and Munetaka Kunishima*

*Faculty of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan, Email: kunisimap.kanazawa-u.ac.jp

K. Yamada, Y. Igarashi, T. Betuyaku, M. Kitamura, K. Hirata, K. Hioki, M. Kunishima, Org. Lett., 2018, 20, 2015-2019.

DOI: 10.1021/acs.orglett.8b00560 (free Supporting Information)


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Abstract

A bench-stable, solid triazine-based oxidizing reagent, 2-hydroperoxy-4,6-diphenyl-1,3,5-triazine (Triazox) can be synthesized from inexpensive starting materials. This reagents has been used for epoxidation of alkenes possessing acid-sensitive functionalities in good to excellent yields. The accompanying nonacidic triazinone coproduct can be easily removed by filtration.

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proposed reaction mechanism



Key Words

epoxidation, 2-hydroperoxy-4,6-diphenyl-1,3,5-triazine


ID: J54-Y2018