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From Antiaromatic Norcorrolatonickel(II) to Aromatic and Nonaromatic Zwitterions: Innocent Ligands with Unbalanced Charge of the Core

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A three-component reaction of antiaromatic meso-mesityl-3-nitronorcorrolatonickel(II) 1-NO2 with dialkyl acetylenedicarboxylate and PBu3 yields aromatic zwitterionic corrole nickel(II) complexes 3-R with one of the meso-substituents comprising a positively charged tributyl phosphonium… Click to show full abstract

A three-component reaction of antiaromatic meso-mesityl-3-nitronorcorrolatonickel(II) 1-NO2 with dialkyl acetylenedicarboxylate and PBu3 yields aromatic zwitterionic corrole nickel(II) complexes 3-R with one of the meso-substituents comprising a positively charged tributyl phosphonium group and negatively charged coordination core. Reaction of 1-NO2 with PBu3 alone resulted in a nonaromatic chiral adduct 5 of a zwitterionic phlorine character with a −PBu3+ group at a pyrrole β-position.

Keywords: aromatic nonaromatic; zwitterions innocent; innocent ligands; antiaromatic norcorrolatonickel; norcorrolatonickel aromatic; nonaromatic zwitterions

Journal Title: Organic Letters
Year Published: 2021

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