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Beilstein J. Org. Chem. 2024, 20, 1221–1235, doi:10.3762/bjoc.20.105
Graphical Abstract
Scheme 1: Reported synthetic methods for the selenation of aromatic compounds.
Scheme 2: Reaction of selenium dioxide with aniline.
Scheme 3: Reaction of selenium dioxide with o-anisidine.
Scheme 4: Reaction of methyl anthranilate with SeO2.
Scheme 5: Reaction mechanism for the formation of diaryl monoselenides.
Scheme 6: Reaction mechanism for the formation of oxamides.
Scheme 7: Reaction mechanism for the formation of quinone 10.
Figure 1: Molecular structure of 3. Thermal ellipsoids drawn at 50% probability. Selected bond lengths (Å): O...
Figure 2: Molecular structure of 9. Thermal ellipsoids drawn at 50% probability. Selected bond lengths (Å): O...
Figure 3: Molecular structure of 13. Thermal ellipsoids drawn at 50% probability. Selected bond lengths (Å): ...
Figure 4: Molecular structure of 10. Thermal ellipsoids drawn at 50% probability. Selected bond lengths (Å) a...
Figure 5: Molecular structure of 11. Thermal ellipsoids drawn at 50% probability. Selected bond angles (°): C...
Figure 6: Molecular structure of 12. Thermal ellipsoids drawn at 50% probability. Selected bond angles (°): C...
Figure 7: Relative energy levels of arylamines and SeO2.
Figure 8: Computationally optimized structure of aniline (a), o-anisidine (b), and methyl anthranilate (c), w...
Scheme 8: Resonance structures for the delocalization of the nitrogen lone pair into the π-system.