BRIDGED OCTAHOMOTETRAOXACALIX[4]ARENES FROM ACYCLIC PRECURSORS

Diols and tetraols obtained by alkylation of the phenolic function of 2,6-bis(hydroxymethyl)-4-methylphenol with mono- or bifunctional elect rophiles, when reacted with the corresponding polybromides in dioxane and heterogeneous KOH or NaOH, gave monocyclic, bicyclic or tricyclic ether derivatives of p-methyloctahomotetraoxacalix(4]arene in fairly g ood yields. Template effects of the alkali metal ion probably operate in the formation of these macropolycyclic polyethers. The obtained tri cyclic compounds are flattened, due to the shortness of the bridging u nits, but the method allows in principle the synthesis of compounds wi th large cavities.