2-Hydroperoxy-4,6-diphenyl-1,3,5-triazine (Triazox) a new epoxidizing reagent
In 2018, M. Kunishima and Coll. published the preparation of 2-hydroperoxy-4,6-diphenyl-1,3,5-triazine (Triazox) as a pure crystalline solid from 2-chloro-4,6-diphenyl-1,3,5-triazine and 30% aqueous H2O2. [1] [2] Triazox has been reported as a bench-stable solid [3] for the epoxidation of alkenes possessing acid-sensitive functionalities as outlined in the Scheme below.
Unlike meta-chloroperoxybenzoic acid (m-CPBA) with the formation of meta-chlorobenzoic acid (pKa 3.82), the non-acidic triazinone by-product formed with Triazox can be easily removed by filtration.
[1] K. Yamada, Y. Igarashi, T. Betuyaku, M. Kitamura, K. Hirata, K. Hioki, M. Kunishima, Org. Lett. 2018, 20, 2015-2019.
[2] I am indebted to my colleague Dr Thomas Glachet from AtlanChim Pharma for calling my attention to this reagent.
[3] No self-accelerating decomposition temperature measurements or thermal stability tests in particular were carried out by the authors.
