Tris(benzocyclobutadieno)benzene, the triangular [4]phenylene with a completely bond-fixed cyclohexatriene ring: cobalt-catalyzed synthesis from hexaethynylbenzene and thermal ring opening to 1,2:5,6:9,10-tribenzo-3,4,7,8,11,12-hexadehydro[12]-annulene

doi:10.1021/JA00271A080

Paper

Tris(benzocyclobutadieno)benzene, the triangular [4]phenylene with a completely bond-fixed cyclohexatriene ring: cobalt-catalyzed synthesis from hexaethynylbenzene and thermal ring opening to 1,2:5,6:9,10-tribenzo-3,4,7,8,11,12-hexadehydro[12]-annulene

Published May 1, 1986 · R. Diercks, K. Vollhardt

Journal of the American Chemical Society

120

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Abstract

1,3,5-cyclohexatriene is commonly introduced in organic textbooks as the hypothetical model for a bond-fixed benzene, yet the search for this structural unit has been elusive. We report two facile approaches to the tris(benzocyclobutadieno)benzene nucleus 1, including the parent 1b, in which the central benzene ring exists in this form, and the first thermal retrocycloaddition of a benzene ring to a trialkyne. Our strategy relies on an iterative sequence of palladium-catalyzed alkynylations followed by cobalt-catalyzed cyclobutabenzoannelations.

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Study Snapshot

This study demonstrates a facile approach to the tris(benzocyclobutadieno)benzene nucleus 1, including the parent 1b, using palladium-catalyzed alkynylations and cobalt-catalyzed cyclobutabenzoanne

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Tris(benzocyclobutadieno)benzene, the triangular [4]phenylene with a completely bond-fixed cyclohexatriene ring: cobalt-catalyzed synthesis from hexaethynylbenzene and thermal ring opening to 1,2:5,6:9,10-tribenzo-3,4,7,8,11,12-hexadehydro[12]-annulene

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