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Synfacts 2009(7): 0733-0733  
DOI: 10.1055/s-0029-1217214
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

More than just Random Mixtures: Synthesis of Higher-Order Oxacalixarenes

Contributor(s): Timothy M. Swager, Ryan M. Moslin
W. Van Rossom, M. Ovaere, L. Van Meervelt, W. Dehaen*, W. Maes
Katholieke Universiteit Leuven, Belgium
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Publication History

Publication Date:
22 June 2009 (online)

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Significance

Building off their earlier work (Org. Lett. 2006, 8, 4161) using nucleophilic aromatic substitution to synthesize oxacalix[2]arene[2]pyr­imidines, the authors communicate a means by which higher-order (6, 8) calixarene derivatives can be made. The reaction is run under kinetic conditions, as longer reaction times and higher temperatures favor the formation of calix[4]arenes, providing 3 and 4 with minimal side products. The products are easily purified using simple silica gel chromatography.