Oligoether-Substituted Derivatives of Carbon-Rich 1,4,7,10,13,16-Hexaethynyltribenzo[a,e,i]cyclododeca-5,11,17-triyne (C36H12) and 1,4,9,12-Tetrakis(ethynyl)dibenzo[a,g]cyclododeca-5,7,13,15-tetrayne (C28H8): Potential Precursors to the Circular [6]Phenylene (‘Antikekulene’) Frame

Uwe Dahlmann; K. Peter C. Vollhardt

doi:10.1055/s-0039-1690050

Synthesis, Inhaltsverzeichnis

Synthesis 2020; 52(08): 1287-1300
DOI: 10.1055/s-0039-1690050

paper

Oligoether-Substituted Derivatives of Carbon-Rich 1,4,7,10,13,16-Hexaethynyltribenzo[a,e,i]cyclododeca-5,11,17-triyne (C₃₆H₁₂) and 1,4,9,12-Tetrakis(ethynyl)dibenzo[a,g]cyclododeca-5,7,13,15-tetrayne (C₂₈H₈): Potential Precursors to the Circular [6]Phenylene (‘Antikekulene’) Frame

Uwe Dahlmann

,

K. Peter C. Vollhardt ∗

Department of Chemistry, University of California at Berkeley, Berkeley, California 94720-1460, USA eMail: kpcv@berkeley.edu

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Abstract

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Abstract

The title compounds, in which the terminal alkyne functions are adorned with -CH₂OCH₂CH₂OCH₂CH₂OCH₂CH₃ or -p-C₆H₄OCH₂CH₂OCH₂CH₂OCH₃ substituents, were synthesized. The strategies for their preparation relied on prior art and involved the use of Sonogashira alkynylations of appropriate haloarenes, Stephens–Castro cyclizations of 1,2,4-trialkynyl-3-iodobenzenes, and Hay oxidative couplings of 1,2,3,4-tetralkynylbenzenes. The targets form yellow materials, exhibiting yellow-green fluorescence, and they are very soluble in polar solvents, but only sparingly so in nonpolar media. Attempts to convert them into the antikekulene frame through CpCo(CO)₂-catalyzed (co)-cyclizations failed.

Key words

alkynes - carbon-rich compounds - cyclotrimerizations - dehydroannulenes - phenylenes

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Referenzen

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