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

Alexandr Fonari; Jens C. Röder; Hao Shen; Tatiana V. Timofeeva; K. Peter C. Vollhardt

doi:10.1055/s-0034-1379140

Synlett, Table of Contents

Synlett 2014; 25(17): 2429-2433
DOI: 10.1055/s-0034-1379140

letter

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

Authors

Alexandr Fonari

^aDepartment of Biology and Chemistry, New Mexico Highlands University, Las Vegas, NM 87701, USA
Jens C. Röder

^bDepartment of Chemistry, University of California at Berkeley, Berkeley, CA 94720-1460, USA Fax: +1(510)6435208 Email: kpcv@berkeley.edu
Hao Shen

^bDepartment of Chemistry, University of California at Berkeley, Berkeley, CA 94720-1460, USA Fax: +1(510)6435208 Email: kpcv@berkeley.edu
Tatiana V. Timofeeva

^aDepartment of Biology and Chemistry, New Mexico Highlands University, Las Vegas, NM 87701, USA
K. Peter C. Vollhardt*

^bDepartment of Chemistry, University of California at Berkeley, Berkeley, CA 94720-1460, USA Fax: +1(510)6435208 Email: kpcv@berkeley.edu

Abstract

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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.

Key words

alkynes - cobalt - cycloaddition - helical structures - polycycles

Full Text

References

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