A Novel Route to Calix[4]arenes. 2. Solution- and Solid-State Structural Analyses and Molecular Modeling Studies

Bruno Botta, Maria Cristina Di Giovanni, Giu Ilano Delle Monache, Maria Cristina De Rosa, Eszter Gacs-Baitz, Maurizio Botta, Federico Corelli, Andrea Tafi, Antonello Santini, Ettore Benedetti, Carlo Pedone, Domenico Misiti

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Abstract

A versatile route to a series of C-alkylcalix[4]resorcinarenes has been developed, using 2,4-dimethoxycinnamates as starting materials under carefully controlled reaction conditions employing BF3 as a Lewis acid catalyst. Depending on the reaction conditions and the nature of the ester side chain in the cinnamates, the calixarenes can adopt 1,2-alternate, 1,3-alternate, or flattened-cone conformational states. An extensive study, relating to the influence of the Lewis acid, temperature, and reaction time, has provided information on the relative ratios of the different conformations and their interconversion. Structural assignments are based on detailed spectroscopic analyses including X-ray analyses. The latter provide evidence of their molecular structure and shape in the solid state. A detailed molecular modeling study has been completed and is described. From the data obtained, good agreement with NMR data, X-ray analyses and experimental results is observed.

Original languageEnglish
Pages (from-to)1532-1541
Number of pages10
JournalJournal of Organic Chemistry
Volume59
Issue number6
DOIs
Publication statusPublished - Mar 1 1994

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ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Botta, B., Di Giovanni, M. C., Monache, G. I. D., De Rosa, M. C., Gacs-Baitz, E., Botta, M., Corelli, F., Tafi, A., Santini, A., Benedetti, E., Pedone, C., & Misiti, D. (1994). A Novel Route to Calix[4]arenes. 2. Solution- and Solid-State Structural Analyses and Molecular Modeling Studies. Journal of Organic Chemistry, 59(6), 1532-1541. https://doi.org/10.1021/jo00085a047