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1.
Chem Commun (Camb) ; 59(25): 3739-3742, 2023 Mar 23.
Article in English | MEDLINE | ID: mdl-36897336

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.

2.
Chem Commun (Camb) ; 58(45): 6510-6513, 2022 Jun 01.
Article in English | MEDLINE | ID: mdl-35575428

ABSTRACT

A 1,3-cycloaddition reaction of 2-(tert-butyl)-8H-isoquinolino[4,3,2-de]phenanthridin-9-ium chloride to NiII norcorrole in the presence of base is shown to produce a family of chiral derivatives of polycyclic system(s) fused with pyrrole subunit(s) of the macrocycle. Dehydrogenation of the cycloaddition products gave rise to dibenzoullazine ortho-fused antiaromatic porphyrinoids.


Subject(s)
Thiosemicarbazones , Azo Compounds , Cycloaddition Reaction , Stereoisomerism
3.
Org Lett ; 23(3): 1032-1037, 2021 Feb 05.
Article in English | MEDLINE | ID: mdl-33475380

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 ß-position.

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