Facile synthesis of thiacalix[n]arenes (n = 4, 6, and 8) consisting of p-tert-butylphenol and methylene/sulfide alternating linkage and metal-binding property of the n = 4 homologue

Noriyoshi Kon, Nobuhiko Iki, Yusuke Yamane, Shin Shirasaki, Sotaro Miyano

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)

Abstract

2,14-Dithiacalix[4]arene 34 was conveniently prepared in 16% yield by acid-catalyzed cyclocondensation of 2,2′-thiobis[4-tert- butylphenol] with formaldehyde. The present method also afforded the first isolation of the analogues with six and eight phenol units, 36 (10%) and 38 (5%), respectively. Solvent extraction showed that 3 4 had high selectivity toward Cu2+ ion at pH5.5 by coordination of the bridging sulfur with cooperative donation of the adjacent phenolate oxygens.

Original languageEnglish
Pages (from-to)207-211
Number of pages5
JournalTetrahedron Letters
Volume45
Issue number1
DOIs
Publication statusPublished - 2004 Jan 1

Keywords

  • Complexation
  • Extraction
  • Sulfide
  • Thiacalixarenes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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