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- Title
Crystalline 2π Aromatic Azadiboriridinylium: A BN Analogue of Cyclopropenylium Cation.
- Authors
Zhu, Lizhao; Kinjo, Rei
- Abstract
N‐Substitution of a thermally unstable diboratriazole 1 with a trimethylsilyl group affords a remarkably stable diboratriazole derivative 2. Ring contraction of 2 with an N‐heterocyclic carbene accompanied by the release of N2 as well as 1,4‐hydrogen shift affords a carbene‐stabilized azadiboriridine 3. Abstraction of the H−B3mem hydride in 3 with methyl trifluoromethanesulfonate leads to the isolation of a hitherto unknown azadiboriridinylium 4, the first BN analogue of cyclopropenylium cation. X‐ray diffraction analysis and computational studies confirmed the delocalization of π electrons over the B2N three‐membered ring, indicating the 2π aromatic feature. Compound 4 undergoes ring expansion reactions with azobenzene and pyridazine to furnish triazadiborolidinylium species 5 and 6, the latter of which possesses a cationic B2N3 ring with a pronounced 6π aromatic property. Moreover, the reaction of 4 with a diazo compound produces a cationic B2N3C pentafulvene derivative 7.
- Subjects
METHYL triflate; CATIONS; DIAZO compounds; PYRIDAZINES; X-ray diffraction; ELECTRONS; AZOBENZENE
- Publication
Angewandte Chemie, 2023, Vol 135, Issue 47, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202312949