Shaping Antiaromatic π‐Systems by Metalation: Synthesis of a Bowl‐Shaped Antiaromatic Palladium Norcorrole. (16th August 2017)

• Record Type: Journal Article
• Authors: Yonezawa, Tsubasa; Shafie, Siham A.; Hiroto, Satoru; Shinokubo, Hiroshi
• Is Part Of: Angewandte Chemie. Volume 129:Number 39(2017)
• Page Start: 11984
• Page End: 11987
• Publication Date: 2017-08-16
• Subjects: Aromatizität -- C-C-Kupplungen -- Gespannte Moleküle -- Porphyrinoide -- Schalenförmige Moleküle; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201706134
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: The synthesis of a bowl‐shaped antiaromatic molecule was achieved through the deformation of a planar antiaromatic porphyrinic π‐conjugation system by insertion of palladium into the small cavity of a metal‐free norcorrole. The bowl‐to‐bowl inversion dynamics of the antiaromatic Pd‐coordinated norcorrole was determined by variable‐temperature 1 H NMR spectroscopy. The metal‐free norcorrole was prepared from acid‐induced demetalation of a copper norcorrole, which was obtained from the intramolecular coupling of a bis(diiododipyrrin) copper complex with copper thiophenecarboxylate.