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Synthesis and Interaction with Copper(II) Cations of Cyano- and Aminoresorcin[4]arenes 1

2002; American Chemical Society; Volume: 67; Issue: 4 Linguagem: Inglês

10.1021/jo010844g

1520-6904

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

Mass Spectrometry Techniques and Applications

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 Cu(II) cations of the new compounds were analyzed by measurements of 1H NMR and EPR spectra in parallel with molecular modeling calculations.