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Synthesis 2001(14): 2105-2112
DOI: 10.1055/s-2001-18065
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Lower Rim Polyhydroxylated Calix[4]arenes

Margarita Seguraa, Francesco Sansoneb, Alessandro Casnatib, Rocco Ungaro*b
a Departamento de Quimica Organica, Facultad de Ciencias, Universidad Autonoma de Madrid, Cantoblanco, 28049, Madrid, Spain
b Dipartimento di Chimica Organica e Industriale dell’Università, Parco Area delle Scienze 17/A, 43100, Parma, Italy
Fax: +39(521)905472; e-Mail: ungaro@unipr.it;
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Publication History

Received 25 June 2001
Publication Date:
09 August 2004 (online)

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Abstract

Several synthetic procedures were evaluated and a protective/deprotective method, which allows the introduction of two, three, and four amide-linked polyhydroxylated units (TRIS) at the lower rim of calix[4]arenes was developed. Di- and trifunctionalized derivatives are poorly soluble in water, whereas the solubility of calix[4]arene having four polyhydroxylated amide groups is good (6 × 10-3 M at 25 °C).

Key words

calixarenes - protecting groups - amides - supramolecular chemistry - water-soluble calix[4]arenes

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