Oxidative insertion of amines into conjugated macrocycles: transformation of antiaromatic norcorrole into aromatic azacorrole
Sha Li, Yahan Sun, Xiaofang Li, Oskar Smaga, Sebastian Koniarz, Miłosz Pawlicki, Piotr J. Chmielewski
Abstract
A new group of aromatic porphyrinoids was obtained by an oxidative insertion of primary amines into the antiaromatic ring of 5,14-dimesityl-norcorrolatonickel(II) activated by iodosobenzene. The substituted 10-azacorroles thus formed were characterized by spectroscopic and electrochemical methods, and XRD analysis. Protonated forms of azacorroles were shown to remain aromatic despite disconnection of the original π-electron delocalization path.
Topics & Concepts
AntiaromaticityConjugated systemChemistryTransformation (genetics)Oxidative phosphorylationAromaticityCombinatorial chemistryOrganic chemistryMoleculePolymerBiochemistryGenePorphyrin and Phthalocyanine ChemistrySynthesis and Properties of Aromatic CompoundsOrganic Electronics and Photovoltaics