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Issue 11, 2005
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Synthesis and capsule formation of upper rim substituted tetra-acrylamido calix[4]arenes

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Abstract

Upper rim substituted tetraiodo calix[4]arenes are coupled to a variety of acrylamides using the palladium catalysed Heck reaction. Tetra-acrylamido upper rim substituted calix[4]arenes are obtained in good yields with exceptionally high stereoselectivity, to produce the all-trans isomers. Tetra-acrylamido calix[4]arenes derived from secondary acrylamides are shown to dimerise via eight hydrogen bonds to form dimeric capsules, which are able to include small organic molecules.

Graphical abstract: Synthesis and capsule formation of upper rim substituted tetra-acrylamido calix[4]arenes

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Article information


Submitted
15 Feb 2005
Accepted
14 Apr 2005
First published
04 May 2005

Org. Biomol. Chem., 2005,3, 2175-2182
Article type
Paper

Synthesis and capsule formation of upper rim substituted tetra-acrylamido calix[4]arenes

N. Kuhnert and A. Le-Gresley, Org. Biomol. Chem., 2005, 3, 2175
DOI: 10.1039/B502378E

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