A "Classical" Tetrahydroxycalix[4]arene Adopting the 1,2-Alternate Conformation

Samah Simaan, Silvio E. Biali*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

26 Scopus citations


The first example of a "classical" tetrahydroxycalixarene, which adopts the 1,2-alternate conformation both in solution and in the crystal, is described. Calixarene derivatives with two distal methylene groups substituted in a trans fashion by phenyl (5a) or mesityl (5b) groups were synthesized via addition of PhMgBr/CuCN or MesMgBr/CuCN to the bis(spirodiene) derivative 3. Whereas the phenyl-substituted calixarene derivative 5a adopts the usual "cone" conformation, solution NMR data and X-ray crystallography indicate that the more crowded mesityl derivative 5b adopts a 1,2-alternate conformation with the two mesityl groups located at isoclinal positions of the macrocycle.

Original languageAmerican English
Pages (from-to)95-98
Number of pages4
JournalJournal of Organic Chemistry
Issue number1
StatePublished - 9 Jan 2004


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