2-Hydroperoxy-4,6-diphenyl-1,3,5-triazine

• 1-Phenyl-1-cyclohexene [P1302]
• 2-Hydroperoxy-4,6-diphenyl-1,3,5-triazine (= Triazox) [H1732]
• 2-Methyl-2-butene [P0067]
• Dichloromethane

To a solution of 1-phenyl-1-cyclohexene (0.300 g, 1.90 mmol), in dichloromethane (10 mL) was added Triazox (0.553 g, 2.08 mmol) at room temperature and the mixture was stirred for 3 hour. The suspension was added 2-methyl-2-butene (2.0 mL, 19.0 mmol) and stirred for 15 minutes at room temperature. The suspension was cooled with ice bath, added hexane (10 mL) and stirred for 5 minutes. The suspension was filtrated and the solvent was removed under reduced pressure. The residue was purified by column chromatography (ethyl acetate:hexane = 1:19 - 1:9 on silica gel), giving compound 1 as a colorless oil (0.297 g, 90%).

The reaction mixture was monitored by TLC (ethyl acetate:hexane = 1:9, Rf = 0.50).

Compound 1

¹H NMR (400 MHz, CDCl₃); δ 7.40-7.23 (m, 5H), 3.08 (m, 1H), 2.33-2.24 (m, 1H), 2.17-2.08 (m, 1H), 2.01-1.95(m, 2H), 1.64-1.41 (m, 3H), 1.36-1.27 (m, 1H).

• An Isolable and Bench-Stable Epoxidizing Reagent Based on Triazine: Triazox
• K. Yamada, Y. Igarashi, T. Betsuyaku, M. Kitamura, K. Hirata, K. Hioki, M. Kunishima, Org. Lett. 2018, 20, 2015.