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Synthesis and cation complexation selectivity of bis(syn-proximally) functionalized calix[4]arenes

✍ Scribed by Jos A. J. Brunink; Willem Verboom; Johan F. J. Engbersen; David N. Reinhoudt; Sybolt Harkema

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
650 KB
Volume
111
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

A general method has been developed for the preparation of bis(syn‐proximally) functionalized calix[4]arenes (6, 8–10). Starting from p‐tert‐butylcalix[4]arene 1a and calix[4]arene 1b syn‐proximally dialkylated calix[4]arenes 2a and 2b, 4, and 5, respectively, were obtained by treatment with 4.2 equiv of NaH and 2.2 equiv of alkylating reagent in DMF. The syn‐proximal substitution pattern was unequivocally proven by an X‐ray structural determination of 2b. Furthermore the influence of different bases on the functionalization of the free hydroxyl groups of 2b with chloroacetone was studied. Cs~2~CO~3~ as the base gave the bis(syn‐proximally) functionalized calix[4]‐arene 6 in the highest yield (82%). Cation complexation studies, with the picrate extraction method, showed that subtle changes in regioselective functionalization influences the selectivity for Na^4^ considerably.

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