Abstract: A convenient method for preparing alkenyloxymethyl crown ethers by cyclization of the corresponding substituted oligoethylene glycols with triethylene glycol ditosylate in high yield is described. The alkenyloxymethyl crown ethers, i.e. γ-allyloxymethyl 15-crown-5 & 18-crown-6, ω-undecenyloxymethyl 15-crown-5 & 18-crown-6, were subjected to hydrosily-lation by triethoxysilane in the presence of tetrakis(triphenylphosphine) platinum complex,followed by immobilization on fumed silica or cohydrolysis with tetraethoxysilane to give the silica-bound polysiloxane-supported 15-crown-5, 18-crown-6, or 15-crown-5, 18-crown-ω-containing silicon resins,respectively.They exhibited high complexation capacities for sodium and potassium picrate and high phase transfer catalytic activity for the anion-promoted nucleophilic substitution of n-nonyl bromide by sodium or potassium iodide.Their complexation capacities and catalytic efficiency depend on the kinds of cation in iodides, the kinds of crown ether, and the length of the spacer group. They also possessed high thermostability.

Key words: Supported crown ether, Alkenyloxymethyl crown other, Polysiloxane, supported crown ether, Complexation capacity, Phase transfer catalysis, Synthesis