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 Cull cations of the new compounds were analyzed by measurements of H-1 NMR and EPR spectra in parallel with molecular modeling calculations.
Synthesis and interaction with copper(II) cations of cyano- and aminoresorcin[4]arenes / Botta, Bruno; G. D., Monache; G., Zappia; Misiti, Domenico; M. C., Baratto; R., Pogni; E., Gacs Baitz; M., Botta; F., Corelli; F., Manetti; A., Tafi. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 67:(2002), pp. 1178-1183. [10.1021/jo010844g]
Synthesis and interaction with copper(II) cations of cyano- and aminoresorcin[4]arenes
BOTTA, Bruno;MISITI, Domenico;
2002
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 Cull cations of the new compounds were analyzed by measurements of H-1 NMR and EPR spectra in parallel with molecular modeling calculations.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
