Preparation and Crystal Structure of the 1,3-alternate Atropisomer of a Calix[4]radialene

Norbert Itzhak, Silvio E. Biali*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

Alkylation of the tetrahydroxy-tetraoxocalix[4]arene 5 with n-butyl bromide proceeds in a stereoselective fashion and affords exclusively a single atropisomer of the tetraoxocalix[4]arene tetrabutyl ether derivative. Reaction with MeLi followed by fourfold acid-catalyzed elimination of water affords the rigid calix[4]radialene 8. The crystal structure of 8 corroborated the proposed calixradialene structure and indicated an 1,3-alternate arrangement of the rings.

Original languageAmerican English
Pages (from-to)3221-3225
Number of pages5
JournalEuropean Journal of Organic Chemistry
Volume2015
Issue number15
DOIs
StatePublished - May 2015

Bibliographical note

Publisher Copyright:
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

  • Calixarenes
  • Cyclophanes
  • Macrocycles
  • Nucleophilic substitution
  • Stereochemistry

Fingerprint

Dive into the research topics of 'Preparation and Crystal Structure of the 1,3-alternate Atropisomer of a Calix[4]radialene'. Together they form a unique fingerprint.

Cite this