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Synlett 2011(3): 396-398  
DOI: 10.1055/s-0030-1259321
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Substituted Linear Ter- and Quaterphenyls via Dewar Benzenes

Štěpánka Jankováa, Simona Hybelbauerováb, Martin Kotora*a,c
a Department of Organic and Nuclear Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 128 43 Praha 2, Czech Republic
Fax: +420(221)951324; e-Mail: kotora@natur.cuni.cz;
b Department of Teaching and Didactics of Chemistry, Faculty of Science, Charles University in Prague, Albertov 3, 128 43 Praha 2, Czech Republic
c Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i., Flemingovo nám. 2, 166 10 Praha 6, Czech Republic
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Publication History

Received 3 November 2010
Publication Date:
13 January 2011 (online)

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Abstract

Tetramethylcyclobutadiene-AlCl3 complex reacted with bisalkynes possessing phenylene and biphenylene spacer giving rise to mono- and bis-Dewar benzenes. The rearrangement of the bis-Dewar benzene derivatives under thermal conditions (150 ˚C) yielded the corresponding linear ter- and quaterphenyl compounds possessing substituted terminal benzene rings. A mixture of an alkynylbiphenyl and a terphenyl was also obtained by the reaction of tetramethylzirconacyclopentadiene with bisalkynylbenzene in 13% combined yield.

Key words

Dewar benzene - alkynes - cyclobutadiene - polycycles - metallacycles

    References and Notes

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