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Synfacts 2007(2): 0159-0159  
DOI: 10.1055/s-2006-955818
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

A Bent Biphenyl Structure Made Through Calix[4]amide Scaffold

Contributor(s): Timothy M. Swager, Yong Yang
M. Tominaga, T. Hatano, M. Uchiyama, H. Masu, H. Kagechika, I. Azumaya*
Tokushima Bunri University, Kagawa, RIKEN, Saitama and Tokyo Medical and Dental University, Japan
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Publication History

Publication Date:
23 January 2007 (online)

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Significance

An iodo-functionalized calix[4]amide is synthesized through the condensation of N,N′-dimethyl-1,3-phenylenediamine with 5-iodoisophthalic acid. This calix[4]amide is found to be exclusively in 1,3-alternate conformation, making the further intramolecular coupling feasible. The single crystal structure of the coupled product indicates the biphenyl moiety possesses hinge angles of 50.1° and 51.7°, and torsion angles of 0.2° and 8.5° (two independent molecules are found in the asymmetric unit).