Synthesis, Structures, and Complexing Abilities of Corands Based on 2-Methoxyresorcinol

Article abstract of DOI:10.1021/jo00265a027

A series of 13 new crown ethers (corands) that bear one or two inward-facing methoxyl groups are synthesized from 2-methoxyresorcinol, and crystal structures of two anisole corands and one bisanisole corand are determined.Demethylation of anisole corands with lithium aluminum hydride affords the corresponding corand phenols, which produce corand quinones upon oxidation by Fremy's salt.Complexing abilities of the corand anisoles, phenols, and quinones for sodium, potassium, and rubidium cations in methanol are assessed by potentiometry, and the electrochemical behavior of the corand quinones and a corand bisquinone is also investigated.