Overcrowded Triply Fused Carbo[7]helicene
Albert Artigas, Florian Rigoulet, Michel Giorgi, Denis Hagebaum‐Reignier, Yannick Carissan, Yoann Coquerel
Abstract
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.
Topics & Concepts
HeliceneChemistryAromaticityCycloadditionRing (chemistry)CatalysisStereochemistryComputational chemistryOrganic chemistryMoleculeSynthesis and Properties of Aromatic CompoundsPhotochromic and Fluorescence ChemistryCyclization and Aryne Chemistry