Extended Calix[8]arenes by Sonogashira Cross-Coupling with Ethynylarenes
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Octabromo and -iodo derivatives of calix[8]arene
were prepared in 85% and 73% yields and structurally
confirmed by NMR, MS and IR spectroscopy and by the formation of
ether or ester derivatives. The octaiodocalix[8]arene
was successfully used in Sonogashira cross-coupling reactions for
the preparation of p-arylethynylcalix[8]arenes.
A single crystal X-ray structure of the starting calix[8]arene 1a shows the molecule in a centrosymmetric conformation,
where four of the six pyridine solvent molecules are H-bonded to
the hydroxyl groups.