Beilstein J. Org. Chem.2024,20, 243–253, doi:10.3762/bjoc.20.24
assumed admixture 11.
Mononitration of compound 5.
Dehydrogenation of compounds 10 and 11.
Nucleophilic methoxylation of compounds 10(12).
Electrophilic bromination of compound 5.
tele-Elimination upon interaction of dibromide 15 with pyrrolidine.
Interaction of dibromide 15 with anionic bases.
Comparison
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Graphical Abstract
Scheme 1:
Comparison of basicity (in water scale) and synthetic availability of quinoline-type azaarenes and ...
Beilstein J. Org. Chem.2019,15, 1996–2002, doi:10.3762/bjoc.15.195
yielding transformations to azide and 1,2,3-triazole derivatives which may have application in other areas of research.
Keywords: calixarene; inherent chirality; mesoionic carbene; mononitration; ruthenacycle; Introduction
Calix[4]arenes are a class of diverse macrocyclic compounds which have been the
the solubility.
An alternative route involving an azide-Sandmeyer reaction on monoaminocalix[4]arene was then envisaged, since the necessary monoaminocalix[4]arene would be accessible via a previously reported mononitration method [28][29][30][31]. However, this method for mononitration of
also important to note was that the reaction did not result in the oxidative bridge formation reported by Lhoták when they attempted a meta-functionalization of a calix[4]arene with palladium. The NMR and mass spectra were proof of this. We have also developed a more robust mononitration method
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Graphical Abstract
Figure 1:
Inherent chirality generated by meta-substitution – the two structures are non-superposable mirror ...