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Calixradialenes: calixarene derivatives with exocyclic double bonds.

Authors
Type
Published Article
Journal
The Journal of Organic Chemistry
1520-6904
Publisher
American Chemical Society
Publication Date
Volume
79
Issue
2
Pages
538–545
Identifiers
DOI: 10.1021/jo402223x
PMID: 24364562
Source
Medline
License
Unknown

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.

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