Calixrotanes: Calixarenes Incorporating Spiro-Linked Cyclopropyl Groups

Ori Shalev, Silvio E. Biali*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

Macrocyclic compounds (calix[4]- and calix[6]arene derivatives) with aryl rings interconnected by spirocyclopropyl groups have been synthesized and structurally characterized. The compounds were prepared by the reaction of dichlorocarbene with calixarenes possessing exocyclic double bonds at the bridges, followed by reductive perdechlorination of the spirocyclopropyl groups. In all systems, pairs of geminal rings connected to the quaternary spiro carbon atoms are oriented anti, and the methylene groups of the cyclopropyl rings are located in isoclinal positions. Calix[6]rotane adopts in the crystal and in solution a 1,3,5-alternate conformation. The presence of the spirocyclopropyl groups increases the rigidity of the macrocyclic ring.

Original languageAmerican English
Pages (from-to)10214-10225
Number of pages12
JournalChemistry - A European Journal
Volume25
Issue number43
DOIs
StatePublished - Aug 2019

Bibliographical note

Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

  • alkenes
  • calixarenes
  • carbenes
  • conformational analysis
  • macrocycles

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