Synthesis of metal-containing tetrolcavitands

ORGN 543

Eric Dueno, eric.dueno@eku.edu, Cesar Zambrano, cesar.zambrano@eku.edu, Jorden Kass, jorden.kass@eku.edu, and Leslie Slasor, leslie.slasor@eku.edu. Department of Chemistry, Eastern Kentucky University, 521 Lancaster Ave., Richmond, KY 40475
The acid catalyzed condensation of resorcinol and acetaldehyde yields the parent resorcenarene. Subsequent bromination of the resorcenarene yielded the tetrabromo derivative. Base catalyzed bridging reaction afforded the cavitand. Nucleophilic attack on methylchloroformate yielded the cavitand tetraester. Subsequent reduction using lithium aluminum hydride afforded the tetrolcavitand. Metal complexation studies of the tetrolcavitand with group IV and group VI transition metals produced new tetra-alkoxy supported complexes in excellent yields (Scheme). These results and the characterization of the metal complexes will be discussed.