Synthesis and Alkali-Metal Complexing Abilities of Crown Ether Tertiary Alcohols

Article abstract of DOI:10.1021/jo00380a012

Twenty-three crown ethers with a hydroxyl and an alkyl or aryl group linked directly to the central carbon of a three-carbon bridge were synthesized in one-step reactions of glycol and bisphenol dianions with substituted 2-(chloromethyl)oxiranes.Crown ether tertiary alcohols with methyl, n-decyl, n-tetradecyl, phenyl, and p-(n-decyl)phenyl substituents and four ring sizes are prepared.The effect of substituent on Na⁺ and K⁺ complexation is assessed by the picrate extraction method for closely related tertiary crown ether alcohols with 16-crown-5 and 15-crown-5-rings.