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Title: A crystalline B₄N₂ dewar benzene as a building block for conjugated B,N-chains
Authors: Ota, Kei
Kinjo, Rei
Keywords: Science::Chemistry
Issue Date: 2021
Source: Ota, K. & Kinjo, R. (2021). A crystalline B₄N₂ dewar benzene as a building block for conjugated B,N-chains. Journal of the American Chemical Society, 143(29), 11152-11159.
Project: MOE2018-T2-048(S)
Journal: Journal of the American Chemical Society
Abstract: Dewar benzene, one of the isolable valence isomers of C6H6, has been extensively studied since its first synthesis in 1962. By contrast, the chemistry of inorganic congeners of Dewar benzene, which can be formally gained by replacing the skeletal carbon atoms with heteroatoms, has been less developed despite their peculiar structural and electronic features. Among them, the extant B,N-Dewar benzenes are limited to the B3N3 system. Herein, we report the development of the first example of an isolable B4N2 Dewar benzene, 3. As predicted by DFT calculations, a judicious selection of the substituents allows synthesizing 3. Single-crystal X-ray analysis, NMR, and computational studies confirmed that 3 possesses a high-lying B(sp3)-B(sp3) σ-bond at the bridgehead position. Reactions with ethylene and phenylacetylene proceeded smoothly under mild conditions, affording the fused B4C4N2 ring systems (4 and 5). Structural characterization as well as DFT calculations revealed that compounds 4 and 5 involve a rigid and conjugated (BN)4 tetraene scaffold. Formation of 4 and 5 demonstrates that 3 may serve as a building block for the construction of conjugated B,N-chains.
ISSN: 0002-7863
DOI: 10.1021/jacs.1c04860
Schools: School of Physical and Mathematical Sciences 
Rights: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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