Upper Rim Substitution of Calixarenes: Carboxylic Acids

Shiv Kumar Sharma; Suseela Kanamathareddy; C. David Gutsche

doi:10.1055/s-1997-1359

Synthesis 1997; 1997(11): 1268-1272
DOI: 10.1055/s-1997-1359

paper

© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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

Abstract

als PDF herunterladen Alle Artikel dieser Rubrik

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

PDF (489 kb)