Synthesis and conformational studies of calixarene analogue chiral [3.3.1]metacyclophanes - Archive ouverte HAL
Article Dans Une Revue Journal of Molecular Structure Année : 2015

Synthesis and conformational studies of calixarene analogue chiral [3.3.1]metacyclophanes

Md Monarul Islam
  • Fonction : Auteur
Tomiyasu Hirotsugu
  • Fonction : Auteur
Taisuke Matsumoto
  • Fonction : Auteur
Junji Tanaka
  • Fonction : Auteur
Takehiko Yamato
  • Fonction : Auteur

Résumé

Trihydroxy[3.3.1]metacyclophane, which can be regarded as an unsymmetrical or incomplete “homocalix[3]arene”, has been prepared from trimethoxy[3.3.1]metacyclophane by demethylation with trimethylsilyl iodide in MeCN. Di-O-methylation at the lower rim of trihydroxy[3.3.1]metacyclophane in the presence of K2CO3 in acetone afforded a novel, inherently chiral calixarene–analogue, namely a macrocyclic [3.3.1]metacyclophane, possessing C1 symmetry. The inherent chirality of the two conformers was characterized by 1H NMR spectroscopy by addition of an excess of Pirkle's chiral shift reagent [(S)-(+)-1-(9-anthryl)-2,2,2-trifluoroethanol], which caused a splitting of the OMe group and AB patterns corresponding to the methylene protons.

Dates et versions

hal-01187783 , version 1 (27-08-2015)

Identifiants

Citer

Md Monarul Islam, Tomiyasu Hirotsugu, Pierre Thuéry, Taisuke Matsumoto, Junji Tanaka, et al.. Synthesis and conformational studies of calixarene analogue chiral [3.3.1]metacyclophanes. Journal of Molecular Structure, 2015, 1098, pp.47-54. ⟨10.1016/j.molstruc.2015.05.036⟩. ⟨hal-01187783⟩
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