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Synfacts 2014; 10(1): 0037
DOI: 10.1055/s-0033-1340394
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Expanded [n]Radialenes: Unusual Carbon-Rich Molecules

Contributor(s):
Timothy M. Swager
,
Derik K. Frantz
Gholami M, Ramsaywack S, Chaur MN, Murray AH, McDonald R, Ferguson MJ, Echegoyen L, Tykwinski RR * University of Erlangen-Nuremberg, Germany; University of Alberta, Edmonton, Canada; Universidad del Valle, Santiago de Cali, Colombia; University of Texas at El Paso, USA
Synthesis and Derivatization of Expanded [n]Radialenes (n = 3, 4).

Chem. Eur. J. 2013;
19: 15120-15132
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Publication History

Publication Date:
13 December 2013 (online)

 
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Key words

expanded radialenes - strained macrocycles - carbon-rich molecules

Significance

Conjugated macrocycles belong to a class of carbon-rich molecules that exhibit unusual structures and fascinating electronic and optical properties. Here, Tykwinski and co-workers report synthetic approaches to extended [4]radialenes 1 and [3]radialenes 2.


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Comment

Synthesis of the extended radialenes 1 and 2 is accomplished by a one-pot deprotection and palladium-catalyzed cross-coupling reaction of common intermediates 3 and 4, respectively. ­Increased bond-angle strain appears to reduce yields in the synthesis of 2 compared to 1. A ­modified synthesis that leads to C 2-symmetric ­expanded [4]radialenes is also presented in this work.


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