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• W2014480608 abstract "The regioselective reaction of resorcarene octaols 1 with 4 equiv of arylsulfonyl chlorides and Et3N in MeCN gives in 30−60% yield the C2v symmetrical tetrasulfonates 3. The mild electrophilic substitution (aminomethylation, bromination) of resorcarene tetrasulfonates 3 and tetraphosphates 2 takes place only in the 2-positions of unsubstituted resorcinol rings yielding distally disubstituted resorcarenes 4. The acylation of hydroxy groups in compounds 2 and 3 gives C2v symmetrical octaesters 5 including large resorcarene tetracrown-ethers. In the minimized boat conformation of tetrasulfonates 3 the two unsubstituted resorcinol rings are vertical and the sulfonyl fragments are arranged in a C2 symmetrical manner via intramolecular SO- - -H−O hydrogen bonds. This structure is proved by NMR and IR spectroscopy. In the case of tetrasulfonate 3c the two enantiomeric conformations interconvert in CDCl3 with ΔG* = 11.6 kcal/mol. This is in agreement with the ΔE* value predicted by molecular mechanics in vacuo." @default.
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• W2014480608 date "1998-11-13" @default.
• W2014480608 modified "2023-10-02" @default.
• W2014480608 title "Synthesis, Conformation, and Binding Properties of Resorcarene Tetrasulfonates. Asymmetric Reorganization of Pendant Sulfonyl Groups via Intramolecular SO- - -H−O Hydrogen Bonds" @default.
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• W2014480608 doi "https://doi.org/10.1021/jo981751a" @default.
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