Novel upper rim functionalizations of calix[4]arenes using the Tscherniac-Einhorn amidomethylation reaction

K.J.C. Bommel, Folke Westerhof, Willem Verboom, David Reinhoudt, A.J.R.L. Hulst

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6 Citations (Scopus)

Abstract

A variety of novel upper rim functionalized calix-[4]arenes have been synthesized, using the Tscherniac-Einhorn amidomethylation reaction. Partially or fully alkylated calix [4]arenes bearing propyl or ethoxyethyl substituents could be easily condensed with various N-methylol-amides and -imides under mild conditions. The resulting methyl-acetamido- (4a, 4b, 7a), methylchloroacetamido (4c, 4d,7b, 7c,9 methylphthalimido (4e, 4f, 4h)and methylchloroacetamido methylphthalimido functionalized calix[4]arenes (5) were obtained in yields varying from 30 till 97%. The amidomethylation reactions were proven to be independent of the conformation of the calix[4]arene.
Original languageUndefined
Pages (from-to)284-290
JournalJournal für praktische Chemie
Volume341
Issue number341
DOIs
Publication statusPublished - 1999

Keywords

  • METIS-105957
  • Calixarenes
  • IR-11026
  • Synthetic methods
  • electrophilic aromatic substitutions
  • amidomethylation
  • C-C coupling

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