An Expedient Synthesis of Ketocalix[6]arene Hexamethyl Ether

Norbert Itzhak, Silvio E. Biali*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

p - tert -Butylcalix[6]arene hexamethyl ether was oxidized in one step to the corresponding ketocalix[6]arene via photochemical bromination (100 W spot lamp) with NBS in a chloroform/water mixture. A pentamethyl ketocalix[6]arene derivative was obtained by reaction of the ketocalix[6]arene hexamethyl ether with boron tribromide dimethyl sulfide complex, and characterized by X-ray crystallography. In the presence of base, the compound undergoes an intramolecular nucleophilic aromatic substitution reaction.

Original languageAmerican English
Pages (from-to)3897-3901
Number of pages5
JournalSynthesis
Volume50
Issue number19
DOIs
StatePublished - 5 Jul 2018

Bibliographical note

Publisher Copyright:
© 2018 Georg Thieme Verlag. All rights reserved.

Keywords

  • bromine
  • calixarenes
  • cleavage
  • ether
  • oxidation
  • phenols

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