Preparation and conformation of dioxocalix[4]arene derivatives

Noa Seri, Iris Thondorf, Silvio E. Biali*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

27 Scopus citations


CrO3 oxidation experiments conducted on atropisomeric forms of 2 (2paco, 21,3-alt and 21,2-alt) indicate that under the reaction conditions only methylene groups located between pairs of geminal rings oriented in an anti disposition are oxidized to carbonyls. NMR data suggest that the tetrahydroxydioxocalix-[4]arenes 7 and 9 adopt the partial cone and 1,2-alternate conformations, respectively. In the crystal structure of 7·2EtOAc the dioxocalixarene adopts a partial cone conformation, whereas 9 adopts in the crystal a 1,2-alternate conformation. In both conformations, pairs of geminal rings connected to a carbonyl are oriented in an anti fashion. The relative stability of the partial cone and 1,2-alternate conformations of 7 and 9 is underestimated by MM3 calculations. The topomerization barriers of 7 and 9 are 12.8 and 13.6 kcal mol-1, respectively.

Original languageAmerican English
Pages (from-to)4774-4780
Number of pages7
JournalJournal of Organic Chemistry
Issue number14
StatePublished - 9 Jul 2004


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