Whereas the synthesis of the anti-cryptophane-A (1) derivative has been known for nearly 40 years, the preparation of its diastereomer (cryptophane-B according to Collet's nomenclature) has never been reported. Thus, the synthesis of the cryptophane-B derivative represents a real challenge for chemists interested in the preparation of these hollow molecules. Herein, we describe a synthetic route that allows us to prepare cryptophane-B (2), albeit in a low yield. The X-ray crystallographic structure of this compound is described, and it reveals the presence of an ethanol molecule inside the cavity of the host. Finally, the ability of cryptophane-B to bind xenon in 1,1,2,2-tetrachloroethane- d is also studied via hyperpolarized Xe NMR.
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Are the Physical Properties of Xe@Cryptophane Complexes Easily Predictable? The Case of - and -Tris-aza-Cryptophanes.
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Laboratoire de Chimie de l'ENS Lyon, (UMR 5182 CNRS-ENS-Université), Université Claude Bernard Lyon 1, F69342 Lyon, France.
Article Synopsis
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Laboratoire de Chimie , Univ Lyon, Ecole Normale Supérieure de Lyon, CNRS UMR 5182, Université Lyon 1, 46 allée d'Italie , Lyon F69364 , France.
Whereas the synthesis of the anti-cryptophane-A (1) derivative has been known for nearly 40 years, the preparation of its diastereomer (cryptophane-B according to Collet's nomenclature) has never been reported. Thus, the synthesis of the cryptophane-B derivative represents a real challenge for chemists interested in the preparation of these hollow molecules. Herein, we describe a synthetic route that allows us to prepare cryptophane-B (2), albeit in a low yield.
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