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 electrophiles, 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 good yields. Template effects of the alkali metal ion probably operate in the formation of these macropolycyclic polyethers. The obtained tricyclic compounds are flattened, due to the shortness of the bridging units, but the method allows in principle the synthesis of compounds with large cavities.