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Synthesis 1997; 1997(11): 1268-1272
DOI: 10.1055/s-1997-1359
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Upper Rim Substitution of Calixarenes: Carboxylic Acids

Shiv Kumar Sharma, Suseela Kanamathareddy, C. David Gutsche*
  • *Department of Chemistry, Texas Christian University, Fort Worth, TX 76129, USA, Fax +1(817)9217330; E-mail: d.gutsche@tcu.edu
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Publication History

Publication Date:
31 December 2000 (online)

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The mono- (5a), bis- (4a and 4b), and tetrakis (1a)-p-cyanomethylcalix[4]arenes as well as the bis(cyanomethyl)calix[6]arene (6a) have been transformed both by acid and base induced hydrolysis to the corresponding p-carboxymethylcalix[4]arenes 5b, 4c, 4d, 2a, and 6b which, in turn, were converted to the methyl (5c, 4e, 4f, 2b) and ethyl (5d, 4g, 2c) esters. The cyanomethyl groups in the sterically hindered compounds 7 and 8 and their corresponding monomers 10 and 11, however, were inert to hydrolysis, even under strenuous conditions. The methyl ester 2b can be converted to the 1,3-dibenzyl ether (3b) and the 1,3-dibenzoate (3c) as well as the tetrabenzyl ether (3a) and tetrabenzoate (3d).

calixarenes - p-cyanomethylcalixarenes - nitrile hydrolysis - etherification - esterification