Synthesis of crown ethers based on a spiro acetal framework

Abstract

A novel class of crown ether derivatives incorporating a 1,7-dioxaspiro[5.5]undecane ring system have been prepared via alkylation of 3,5-diaxial diol 4 with polyethylene glycol ditosylates [di(toluene-p-sulfonates)]. The complexing properties of these crown ethers with alkali metal cations and ammonium ion have been evaluated using Cram’s picrate extraction method. Crown ethers 1, 2 show a higher affinity for potassium ion than 18-crown-6 exhibits.