Unprecedented cyclisations of calix[4]arenes under the Mitsunobu protocol. Part 3: Thiacalix[4]crowns versus dimers

Viktor Csokai, Barbara Balázs, Gábor Tóth, Gyula Horváth, István Bitter

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

Intermolecular couplings versus intramolecular ring closures were observed in the reaction of p-tert-butylthiacalix[4]arene and diethylene glycols affording dimers 2 and/or the inherently chiral 1,2-thiacalix[4]crown-3 derivatives 5 under the Mitsunobu protocol. The enantiomeric separation of 5a was achieved by chiral HPLC. The reaction of thiacalix[4]monocrowns 1 with diethylene glycols failed to give crowned thiacalix-tubes 7, instead biscrowns 8 were formed. Partially alkylated double thiacalix[4]arenes 10, 11 were obtained via the base promoted alkylations of a thiacalixarene dimer 2a containing diethyleneoxy linkers. Graphical Abstract

Original languageEnglish
Pages (from-to)12059-12066
Number of pages8
JournalTetrahedron
Volume60
Issue number52
DOIs
Publication statusPublished - Dec 20 2004

Keywords

  • Cyclisations
  • Dimers
  • Mitsunobu reaction
  • Thiacalix[4]arenes
  • Thiacalix[4]crowns

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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