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Synthesis of Substituted Linear Ter- and Quaterphenyls via Dewar Benzenes

Publication at Faculty of Science |
2011

Abstract

Tetramethylcyclobutadiene-AlCl(3) 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 degrees 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.