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Synlett 2014; 25(17): 2429-2433
DOI: 10.1055/s-0034-1379140
DOI: 10.1055/s-0034-1379140
letter
Toward Antikekulene: Angular 1,2-Di-, 2,3-Di-, and 1,2,15,16-Tetrachloro[6]phenylene
Further Information
Publication History
Received: 16 June 2014
Accepted after revision: 20 August 2014
Publication Date:
17 September 2014 (online)
Abstract
The synthesis of the first ring-functionalized heliphenes is described, comprised of angular 1,2-di-, 2,3-di-, and 1,2,15,16-tetrachloro[6]phenylene, via a series of Sonogashira couplings and cobalt-catalyzed alkyne cyclotrimerization steps. These molecules are explored as potential precursors to antikekulene and their reactivity compared to that of the parent angular [6]phenylene. An X-ray structural determination of 1,2,15,16-tetrachloro[6]phenylene reveals a structure with a considerably larger helical separation than in [6]phenylene, caused by the bulk of the appended chlorine atoms.
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- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000083.
- Supporting Information
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