Fig. 2. Optimization of the reaction conditions for the uncatalyzed aerobic epoxidation reaction of alkenes.
A Results for the epoxidation reaction of alkenes 1b–h under 4 bar of O2 in a glass autoclave reactor at 100 °C for 18 h. B Results for the epoxidation reaction of alkene 1b at 130 °C under the reaction conditions of (A) and in the presence or not of a metal nut. C Results for the epoxidation reaction of alkenes 1b and 1f after bubbling O2 through the neat alkene at 130 °C for 18 h. D Kinetic plot for the epoxidation reaction of alkene 1f in a round-bottomed flask with O2 bubbling at 200 °C. E Results for the epoxidation reaction of alkenes 1b, 1f, and 1g under reaction conditions in (D) (open flask) at different temperatures. F Results for the epoxidation reaction of alkenes 1b and 1f under 65 bar of diluted (5%) O2 in N2, in a TeflonTM vessel within an autoclave reactor at 130 °C for 18 h. All results refer to gas chromatography (GC) yields, tripled checked mass spectrometry (GC–MS), 1H nuclear magnetic resonance (1H NMR), and isolated yield after purification by flash column chromatography.
