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Title: Synthesis of Calix[4]arenes. 5. Design, Synthesis and Computational Studies of Chiral Amidoresorc[4]arenes
Authors: B., Botta
G., Delle Monache
M. C., De Rosa
C., Seri
E., Benedetti
R., Iacovino
Botta, Maurizio 
Corelli, Federico 
V., Masignani
Tafi, Andrea 
E., Gacs Baitz
A., Santini
D., Misiti
Issue Date: 1997
Project: None 
Treatment of tetraaIcohol 1 with glutaroyl (2a, n = 3), adipoyl (2b, n = 4), and pimeloyl (2c, n = 5) dichlorides in the presence of Et(3)N gave the corresponding double-spanned calix[4]resorcarenes 3a-c, in which the insertion of two polymethylene bridges led to the formation of a cavity-shaped architecture resembling a basket. NMR, X-ray, and molecular dynamic-studies showed that one of the two equivalent flattened-cones, which constituted the original cone conformation of 1, had been frozen in the basket derivative. In the solid state the calixarene 3b exists as a supramolecular dimer, in which one of the handles is inserted in the concave cavity of an adjacent molecule. A molecular modeling study revealed that the minimum absolute free energy was associated to the unsymmetrical type of dimer named AB-AC.
ISSN: 0022-3263
DOI: 10.1021/jo9619692
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