Conformation and Stereodynamics of Monodioxamethylene Calix[4]arene Derivatives

Jens Wöhnert, Jörg Brenn, Matthias Stoldt, Oleg Aleksiuk, Flavio Grynszpan, Iris Thondorf*, Silvio E. Biali

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

13 Scopus citations


Reaction of the monospirodienone derivative of p-tert-butylcalix[4]arene with methylene chloride/base in the presence of a phase transfer catalyst yielded the bridged monodioxamethylene derivative 6 which was characterized by X-ray crystallography. Treatment of 6 with NaBH4 resulted in exo-reduction of the carbonyl group and afforded the spiro alcohol 7, which rearranged thermally to the monodioxamethylene bridged calix[4]arene 3. Calixarene 3 exists in solution (CD2Cl2, 198 K) in three different conformations (a cone form with the dioxocine unit in a distorted boat conformation, and cone and partial cone forms with a boat-chair arrangement of the dioxocine) which interconvert with barriers in the 13.5-14.3 kcal mol-1 range. Molecular mechanics calculations indicate that the rate-limiting steps for the conformational interconversions of 3 involve transitions of the dioxocine subunit.

Original languageAmerican English
Pages (from-to)3866-3874
Number of pages9
JournalJournal of Organic Chemistry
Issue number12
StatePublished - 12 Jun 1998


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