Synthesis of Cryptophane-B. Crystal Structure and Study of its Complex with Xenon.

Thierry Brotin (1) , Erwann Jeanneau (2) , Patrick Berthault (3) , Estelle Léonce (3) , Delphine Pitrat (1) , Jean-Christophe Mulatier (1)

1 LC - Laboratoire de Chimie - UMR5182
2 UCBL - Université Claude Bernard Lyon 1
3 LSDRM - Laboratoire Structure et Dynamique par Résonance Magnétique (LCF)

Whereas the synthesis of the $anti$-cryptophane-A (1) derivative is 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), however in 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 $^{129}$Xe NMR

Domains: Material chemistry; Organic chemistry; Analytical chemistry

Thierry Brotin, Erwann Jeanneau, Patrick Berthault, Estelle Léonce, Delphine Pitrat, et al.. Synthesis of Cryptophane-B. Crystal Structure and Study of its Complex with Xenon.. Journal of Organic Chemistry, 2018, 83, pp.14465-14471. ⟨10.1021/acs.joc.8b02246⟩. ⟨cea-01922217⟩