Contribution of Lipophilicity to the Performance of Crown Ethers. Effect of Bulk and Shape of the Lipophilic Substituents

Article abstract of DOI:10.1021/jo00147a021

15-Crown-5 and 18-crown-6 ethers bearing substituents on the ether ring have been studied as catalysts for the Finkelstein reaction and as agents for solubilization of alkali metal picrates in n-heptane.All of these substituted crown ethers form stable complexes with Na⁺ and K⁺.These with highly lipophilic substituents are much more effective than the parent unsubstituted crown ethers as catalysts and as solubilizing agents.Both types of activity are affected by the bulk and the shape of the lipophilic substituent.