Synthesis of dibenzo-16-crown-5 compounds with pendant ester and ether groups

Structurally related dibenzo-16-crown-5 lariat ethers with pendant ester and ether groups are prepared. Structural variations within the series of alkyl lariat ether esters include changes in the O-alkyl group, attachment site and nature of the lipophilic group, and length of the spacer, which connects the ester group to the polyether framework. Also synthesized are bis(crown ether) diesters with two dibenzo-16-crown-5 or two dicyclohexano-16-crown-5 units and two ester groups connected to each other by a linker of varying length. Synthetic strategies for the preparation of these lariat ethers with pendant ester- and ether-containing side arms are described.