Synthesis of hexahomotrioxacalix[3]naphtalenes and a study of their alkali-metal cation binding properties

M Ashram; S Mizyed; P E Georghiou

doi:10.1021/jo001518o

Synthesis of hexahomotrioxacalix[3]naphtalenes and a study of their alkali-metal cation binding properties

J Org Chem. 2001 Feb 23;66(4):1473-9. doi: 10.1021/jo001518o.

Authors

M Ashram¹, S Mizyed, P E Georghiou

Affiliation

¹ Department of Chemistry, Memorial University of Newfoundland, St. John's, Newfoundland A1B 3X7, Canada.

PMID: 11312982
DOI: 10.1021/jo001518o

Abstract

The first syntheses of the C3-symmetrical and unsymmetrical hexahomotrioxacalix[3]naphthalenes 3 and 4, respectively, and the corresponding tert-butyl hexahomotrioxacalix[3]naphthalene 3a are reported. A convergent synthesis of the linear hexahomotrimer precursors 19 and 19a is described, but the direct synthesis of 3 and 3a can also be achieved from the monomers 20 and 20a, respectively. A limited study of the binding properties of alkali-metal cations by 3 or 3a using a picrate-CHCl3 extraction showed only weak abilities to bind with the cations examined.