Synthesis and Reactions of Calix[4]arene Bisanhydrides1

The tetrabenzyl ether, tetra-p-bromobenzenesulfonate, and tetra-p-methylbenzenesulfonate of p-carboxymethylcalix[4]arene in the 1,3-alternate conformation have been converted to the corresponding bisanhydrides. Reactions of the bisanhydrides with alcohols or amines afford calix[4]arenes carrying two...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 64; no. 10; pp. 3507 - 3512
Main Authors Sharma, Shiv Kumar, Gutsche, C. David
Format Journal Article
LanguageEnglish
Published American Chemical Society 14.05.1999
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Summary:The tetrabenzyl ether, tetra-p-bromobenzenesulfonate, and tetra-p-methylbenzenesulfonate of p-carboxymethylcalix[4]arene in the 1,3-alternate conformation have been converted to the corresponding bisanhydrides. Reactions of the bisanhydrides with alcohols or amines afford calix[4]arenes carrying two carboxymethyl and two carboalkoxymethyl or two amidomethyl groups on the upper rim positions. The substitution pattern that is established confers molecular chirality on the calixarenes.
Bibliography:istex:FCDAF79531E1E532BCD2B987306B84F607BB8CED
ark:/67375/TPS-SKD9LZW9-J
ISSN:0022-3263
1520-6904
DOI:10.1021/jo9822636