Synthesis of Cryptophane-B: Crystal Structure and Study of Its Complex with Xenon
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 chemi...
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| Veröffentlicht in: | Journal of organic chemistry 2018-12, Vol.83 (23), p.14465-14471 |
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| container_issue | 23 |
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| container_title | Journal of organic chemistry |
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| creator | Brotin, Thierry Jeanneau, Erwann Berthault, Patrick Léonce, Estelle Pitrat, Delphine Mulatier, Jean-Christophe |
| description | 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 2 is also studied via hyperpolarized 129Xe NMR. |
| doi_str_mv | 10.1021/acs.joc.8b02246 |
| format | Article |
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| ispartof | Journal of organic chemistry, 2018-12, Vol.83 (23), p.14465-14471 |
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| source | ACS Publications |
| subjects | Analytical chemistry Chemical Sciences Material chemistry Organic chemistry |
| title | Synthesis of Cryptophane-B: Crystal Structure and Study of Its Complex with Xenon |
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