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- Title
The Triboracyclopropenyl Dianion: The Lightest Possible Main-Group-Element Hückel π Aromatic.
- Authors
Kupfer, Thomas; Braunschweig, Holger; Radacki, Krzysztof
- Abstract
Hückel π aromaticity is typically a domain of carbon-rich compounds. Only very few analogues with non-carbon frameworks are currently known, all involving the heavier elements. The isolation of the triboracyclopropenyl dianion is presented, a boron-based analogue of the cyclopropenyl cation, which belongs to the prototypical class of Hückel π aromatics. Reduction of Cl2BNCy2 by sodium metal produced [B3(NCy2)3]2-, which was isolated as its dimeric Na+ salt (Na4[B3(NCy2)3]2·2 DME; 1) in 45% yield and characterized by single-crystal X-ray diffraction. Cyclic voltammetry measurements established an extremely high oxidation potential for 1 (Epc=-2.42 V), which was further confirmed by reactivity studies. The Hückel-type π aromatic character of the [B3(NCy2)3]2- dianion was verified by various theoretical methods, which clearly indicated π aromaticity for the B3 core of a similar magnitude to that in [C3H3]+ and benzene.
- Subjects
DIANIONS; CARBON compounds; CYCLOPROPENE; AROMATIZATION; CYCLIC voltammetry; AROMATICITY; HUCKEL molecular orbitals; BENZENE
- Publication
Angewandte Chemie International Edition, 2015, Vol 54, Issue 50, p15084
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201508670