Synlett 2014; 25(17): 2429-2433
DOI: 10.1055/s-0034-1379140
letter
© Georg Thieme Verlag Stuttgart · New York

Toward Antikekulene: Angular 1,2-Di-, 2,3-Di-, and 1,2,15,16-Tetrachloro[6]phenylene

Alexandr Fonari
a   Department of Biology and Chemistry, New Mexico Highlands University, Las Vegas, NM 87701, USA
,
Jens C. Röder
b   Department of Chemistry, University of California at Berkeley, Berkeley, CA 94720-1460, USA   Fax: +1(510)6435208   Email: kpcv@berkeley.edu
,
Hao Shen
b   Department of Chemistry, University of California at Berkeley, Berkeley, CA 94720-1460, USA   Fax: +1(510)6435208   Email: kpcv@berkeley.edu
,
Tatiana V. Timofeeva
a   Department of Biology and Chemistry, New Mexico Highlands University, Las Vegas, NM 87701, USA
,
K. Peter C. Vollhardt*
b   Department of Chemistry, University of California at Berkeley, Berkeley, CA 94720-1460, USA   Fax: +1(510)6435208   Email: kpcv@berkeley.edu
› Author Affiliations
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.

Supporting Information

 
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