Preparation of crown ethers with isoxazolyl-lariats: Homologation of isoxazole aldehydes, and a critical comparison of lariat functional moieties for lanthanide extraction

Xiong Bing Xia, Mark S. Munsey, Hongshan Du, Chien M. Wai, Nicholas R. Natale

Research output: Contribution to journalArticlepeer-review

Abstract

A critical comparison of several lariat ether functional moieties is presented. The synthesis of two isoxazolyl-lariat ethers is described. The lariat ether (2, n = 1) undergoes β-fragmentation on electron transfer reductive ring-opening with samarium diiodide. The isoxazole moiety was then homologated to overcome this problem, and isoxazole lariat ether (2, n = 3) was obtained. The isoxazole (2, n = 3) and β-diketone (3, n = 3) crowns were evaluated in lanthanide shift studies and liquid-liquid extraction studies. Finally, lateral metalation and electrophilic quenching with carbon dioxide produced the carboxylic acid (12) which proved to be an efficient ligand for the liquid-liquid extraction of lanthanides.

Original languageEnglish
Pages (from-to)711-722
Number of pages12
JournalHeterocycles
Volume32
Issue number4
DOIs
StatePublished - Apr 1 1991

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