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

Md Monarul Islam, Tomiyasu Hirotsugu, Pierre Thuery, Taisuke Matsumoto, Junji Tanaka, Mark R.J. Elsegood, Carl Redshaw, Takehiko Yamato

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16 Citations (Scopus)


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.

Original languageEnglish
Pages (from-to)47-54
Number of pages8
JournalJournal of Molecular Structure
Publication statusPublished - Jun 12 2015

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry


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