Calixradialenes: Calixarene derivatives with exocyclic double bonds

David Poms, Norbert Itzhak, Lev Kuno, Silvio E. Biali*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

Reaction of dioxocalix[4]arene 7 with MeLi followed by 2-fold elimination of water yielded calixarene 8 possessing exocyclic double bonds at two adjacent bridges. Calixarene 8 exists in tetrachloroethane-d2 solution at rt, as a 2.3:1 mixture of the 1,3-alternate and partial cone conformers. Keto[n]calixarenes (n = 5, 6) were prepared via hydrolysis of the bromocalixarenes 11 and 12, followed by CrO3 oxidation of the respective hydroxymethylene derivatives. Addition of MeLi to the ketocalix[n]arenes (n = 4, 5 and 6) followed by elimination of water yielded the corresponding calix[n]radialenes. Calix[5]- and calix[6]radialenes adopt in the crystal irregular alternate (i.e., noncone) conformations.

Original languageAmerican English
Pages (from-to)538-545
Number of pages8
JournalJournal of Organic Chemistry
Volume79
Issue number2
DOIs
StatePublished - 17 Jan 2014

Fingerprint

Dive into the research topics of 'Calixradialenes: Calixarene derivatives with exocyclic double bonds'. Together they form a unique fingerprint.

Cite this