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Beilstein J. Org. Chem. 2022, 18, 660–668, doi:10.3762/bjoc.18.67
Graphical Abstract
Scheme 1: Synthesis of cyclochexene oxide via epoxidation with air in the presence of isobutyraldehyde.
Figure 1: Epoxidation of cyclohexene with air bubbling in batch at various temperature.
Figure 2: Schematic diagram (a) and photo (b) of the flow reactor used for cyclohexene epoxidation with air. ...
Figure 3: Investigation of reaction temperature in flow epoxidation of cyclohexene at residence time of 0.35 ...
Figure 4: Investigation of residence time in flow epoxidation of cyclohexene at 100 °C.
Scheme 2: Plausible reaction pathway of the epoxidation of cyclohexene with air in the flow system.
Figure 5: Continuous production of cyclohexene oxide.
Figure 6: Effect of concentration of cyclohexene and eqivalent of aldehyde.
Beilstein J. Org. Chem. 2018, 14, 1192–1202, doi:10.3762/bjoc.14.100
Scheme 1: Generation and reaction of cationic species generated by “indirect cation pool” methods.
Figure 1: (a) 1H NMR of N-acyliminium ion C1 in CD2Cl2 at −80 °C (600 MHz). (b) Preferred conformation of C1.
Figure 2: (a) 1H NMR spectrum of C3 in CD2Cl2 at −60 °C (400 MHz). (b) Preferred conformation of C3.
Figure 3: (a) 1H NMR spectrum of C5 in CD2Cl2 at −60 °C (400 MHz). (b) Preferred conformation of C5.
Figure 4: Summary of the conformations of N-acyliminium ions C1–C6.
Figure 5: Stevens’ hypothesis on the tendency of the addition of nucleophiles to N-acyliminium ions. The subs...
Figure 6: A plausible mechanism of the observed diastereoselective reaction of the N-acyliminium ions.
Figure 7: Comparison of ΔG for the pseudo-equatorial and pseudo-axial conformations of C1–C6 at the B3LYP/6-3...