Calix[4]arenes with a lid in their upper rims: 1,3-Dipolar cycloaddition reactions of benzonitrile oxides with 5-allyl-, 5,11-dially- and 5,17-diallylcalix[4]arenes

Chun Mei Shu*, Wei Ling Lin, Gene Hsiang Lee, Shie Ming Peng, Wen-Sheng Chung

*Corresponding author for this work

Research output: Contribution to journalArticle

15 Scopus citations

Abstract

The upper rim substituted mono- and diisoxazolinomethylcalix[4]arenes 9-23 are synthesized in good yields from 1,3-dipolar cycloaddition reactions of para-substituted phenyl nitrileoxides with 5-allyl-, 5,11-diallyl- and 5,17-diallycalix[4]arenes 5-7; the structures of 9-23 are consistent with a 'cone' conformation and the 'vase-with-a-lid' structure of 11 was confirmed by a single-crystal x-ray analysis. Preliminary results show that the monoisoxazolinomethylcalix[4]arene can form an inclusion complex with ammonium cation.

Original languageEnglish
Pages (from-to)173-182
Number of pages10
JournalJournal of the Chinese Chemical Society
Volume47
Issue number1
DOIs
StatePublished - 1 Jan 2000

Keywords

  • 1,3-dipolar
  • Calix[4]arene
  • Claisen rearrangement
  • Isoxazoline
  • Nitrile oxides

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