Overcrowded Triply Fused Carbo[7]helicene.

J Am Chem Soc

Aix Marseille Univ, CNRS, Centrale Marseille, ISM2, 13397 Marseille, France.

Published: July 2023

This paper presents the synthesis and comprehensive analysis of a highly contorted and doubly negatively curved multihelicene compound, composed of three carbo[7]helicene units fused within a central six-membered ring. The synthesis of this compound involved a [2 + 2 + 2] cycloaddition reaction of 13,14-picyne, employing a Ni(0) catalyst, which exhibited superior performance compared to conventional Pd(0) catalysts. The evaluation of aromaticity in this triple carbo[7]helicene, utilizing magnetic and electronic criteria, led to noteworthy insights challenging the limitations of Clar's model of aromaticity.

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http://dx.doi.org/10.1021/jacs.3c05415DOI Listing

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Overcrowded Triply Fused Carbo[7]helicene.

J Am Chem Soc

July 2023

Aix Marseille Univ, CNRS, Centrale Marseille, ISM2, 13397 Marseille, France.

This paper presents the synthesis and comprehensive analysis of a highly contorted and doubly negatively curved multihelicene compound, composed of three carbo[7]helicene units fused within a central six-membered ring. The synthesis of this compound involved a [2 + 2 + 2] cycloaddition reaction of 13,14-picyne, employing a Ni(0) catalyst, which exhibited superior performance compared to conventional Pd(0) catalysts. The evaluation of aromaticity in this triple carbo[7]helicene, utilizing magnetic and electronic criteria, led to noteworthy insights challenging the limitations of Clar's model of aromaticity.

View Article and Find Full Text PDF

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