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Chloride-Templated Macrocyclization and Anion-Binding Properties of C2-Symmetric Macrocyclic Ureas from Sucrose
Katarzyna Łęczycka-Wilk1, Kajetan Dąbrowa1, Piotr Cmoch1
1Institute of Organic Chemistry, Polish Academy of Sciences , Kasprzaka 44/52, 01-224 Warsaw, Poland.
Abstract:
A high-yielding, one-pot simultaneous synthesis and full characterization of two regioisomeric C2-symmetrical macrocycles 3a and 3b from triphosgene and readily available hexa-O-benzyl-6,6'-diaminosucrose 1 is reported. The efficient macrocyclization (90% overall yield, ∼1:1 ratio of 3a vs 3b) is attributed to favorable steric constraints and to a templation by a chloride anion. 1H NMR titration studies and theoretical predictions revealed that both receptors show similar affinity for acetate and benzoate anions and enhanced preference for chloride over H2PO4-.
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