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Synfacts 2008(4): 0370-0370  
DOI: 10.1055/s-2008-1042846
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Highly Bent Pyrenophanes

Contributor(s): Timothy M. Swager, Jan M. Schnorr
B. Zhang, G. P. Manning, M. A. Dobrowolski, M. K. CyraÑski, G. J. Bodwell*
Memorial University, St. John’s, Canada and University of Warsaw, Poland
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Publication History

Publication Date:
19 March 2008 (online)

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Significance

Cyclophanes that consist solely of arylene units are interesting from the macrocycle as well as the cyclophane perspective. The authors report the synthesis of the highly bent pyrenophane 6 as well as its counterpart without phenyl groups. The former was obtained starting from 5-hydroxyisophthalic acid 1 which was converted into 3 via tetraesterdiyne 2 in eight steps. The following transformation to the dithiacyclophane 4 could be performed in 83% yield. Bridge contraction, double-bond formation and VID reaction led to the final product 6 in 1.6% overall yield.