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Synfacts 2015; 11(1): 0031
DOI: 10.1055/s-0034-1379667
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Twin Helicenes Twist Benzene

Contributor(s):
Timothy M. Swager
,
Kathleen R. White
Hashimoto S, Nakatsuka S, Nakamura M, * Hatakeyama T. * Kwansei Gakuin University, Hyogo, Kyoto University, and Japan Science and Technology Agency, Tokyo, Japan
Construction of a Highly Distorted Benzene Ring in a Double Helicene.

Angew. Chem. Int. Ed. 2014;
53: 14074-14076
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Further Information

Publication History

Publication Date:
15 December 2014 (online)

 
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Key words

aromaticity - helical structures - ligand design - Friedel–Crafts reaction

Significance

The authors report a new approach to construct distorted benzene rings by constraining a benzene ring between two opposing [5]helicenes. Double helicene 5 was synthesized via a tandem intramolecular phospha-Friedel–Crafts reaction. By X-ray crystallography, the central benzene ring of 5 was found to possess a bending angle of 23°, and the sulfur atoms were found to be in a cis arrangement.


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Comment

Distorted double helicene 5 can be desulfurized with triethylphosphine to yield bis(phosphine) 7, which could find potential use as a C 2-symmetric ligand for bimetallic complexes, following separation of enantiomers.


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