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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19. März 2008 (online)


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.