Optimization of phase-transfer catalysts designed from calix[4]arene

Koji Araki, Akihiro Yanagi, Seiji Shinkai

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

To optimize the calix[4]arene structure for a phase-transfer catalyst, we modified the upper rim with lipophilic tert-octyl groups and the lower rim with O(CH2CH2O)mMe (m=1, 2, and 3). Through two-phase solvent extraction, 1H NMR studies on the metal-binding site, and phase-transfer catalysis we have reached conclusions that (i) lipophilic groups introduced into the upper rim effectively enhance the catalytic activity whereas (ii) to compose an effective ionophoric cavity on the lower rim, OCH2CH2OMe (i.e., m=1) suffices and m=2 and m=3 rather decrease the catalytic activity and cause emulsification. The optimized calix[4]arene-based phase-transfer catalyst showed the catalytic activity comparable with dicyclohexyl-18-crown-6.

Original languageEnglish
Pages (from-to)6763-6772
Number of pages10
JournalTetrahedron
Volume49
Issue number31
DOIs
Publication statusPublished - Jul 30 1993

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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