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Synfacts 2008(2): 0154-0154  
DOI: 10.1055/s-2007-992420
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Planar [6]Radialenes

Contributor(s): Timothy M. Swager, Koushik Venkatesan
A. Patra, Y. H. Wijsboom, L. J. W. Shimon, M. Bendikov*
Weizmann Institute of Science, Rehovot, Israel
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Publication History

Publication Date:
23 January 2008 (online)

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Significance

The authors report an efficient synthesis and structural characterization of previously unknown benzo[1,2-c:3,4-c′:5,6-c′′]triseleno­phene 2 and its known sulfur analogue, benzo[1,2-c:3,4-c′:5,6-c′′]trithiophene 1. They also report previously unknown selenophene-fused [8]annulene 4 and its known sulfur analogue 3. The coupling of 3,4-dibromothiophene with [Ni(cod)2] in the presence of 1,5-cyclooctadiene (cod) and the neutral ligand Ph3P in dry acetonitrile produced compounds 1 and 3 in a 1:1 ratio. Reaction of 3,4-dibromoselenophene in a similar fashion yielded the selenium analogues 2 and 4 in 5:1 ratio.