Synthesis and interaction with copper(II) cations of cyano- and aminoresorcin[4]arenes

Bruno Botta, Giuliano Delle Monache, Giovanni Zappia, Domenico Misiti, Maria Camilla Baratto, Rebecca Pogni, Eszter Gacs-Baitz, Maurizio Botta, Federico Corelli, Fabrizio Manetti, Andrea Tafi

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Abstract

Following our studies on resorcin[4]arenes, we synthesized new macrocycles containing cyanomethyl and aminomethyl side chains. Three stereoisomers (2a-c) of the former were obtained by BF3·Et2O tetramerization of the corresponding trans-cinnamic acid derivative and were shown to be in the 1,2-alternate, cone, and 1,3-alternate conformations. Conversely, the tetraamino derivative 6a in the cone conformation was prepared from the corresponding tetrabromide 3a. The interactions with CuII cations of the new compounds were analyzed by measurements of 1H NMR and EPR spectra in parallel with molecular modeling calculations.

Original languageEnglish
Pages (from-to)1178-1183
Number of pages6
JournalJournal of Organic Chemistry
Volume67
Issue number4
DOIs
Publication statusPublished - Feb 22 2002

ASJC Scopus subject areas

  • Organic Chemistry

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    Botta, B., Delle Monache, G., Zappia, G., Misiti, D., Baratto, M. C., Pogni, R., Gacs-Baitz, E., Botta, M., Corelli, F., Manetti, F., & Tafi, A. (2002). Synthesis and interaction with copper(II) cations of cyano- and aminoresorcin[4]arenes. Journal of Organic Chemistry, 67(4), 1178-1183. https://doi.org/10.1021/jo010844g