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Synfacts 2009(5): 0500-0500  
DOI: 10.1055/s-0029-1216568
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Heterofunctionalized Calixarenes via Intramolecular Aryl Aminations

Contributor(s): Timothy M. Swager, Ryan M. Moslin
K. V. Lawson*, A. C. Barton, J. D. Spence*
California State University, Sacramento, USA
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Publication History

Publication Date:
22 April 2009 (online)

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Significance

The authors generate azacalix­arenes using an intramolecular aryl amination as ring-closing step. Using this technique, they produced the first examples of 4-tert-butylcalix[n]-arenes (n = 8, 12) with selective substitution of bridging methylenes with amines. The technique represents a macrocyclic dimerization (2) and ­trimerization (3) of the starting material 1. The ­authors could not obtain the monomeric macro­cyclization regardless of the dilution conditions.