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Dewar benzene, one of the isolable valence isomers of C 6 H 6 , 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 B 3 N 3 system. Herein, we report the development of the first example of an isolable B 4 N 2 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 tha 3 possesses a high-lying B(sp 3 )-B(sp 3 ) σ-bond at the bridgehead position. Reactions with ethylene and phenylacetylene proceeded smoothly under mild conditions, affording the fused B 4 C 4 N 2 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 etraene scaffold. Formation of 4 and 5 demonstrates tha 3 may serve as a building block for the construction of conjugated B,N-chains.

A Crystalline B4N2 Dewar Benzene as a Building Block for Conjugated B,N-Chains

A Crystalline B₄N₂ Dewar Benzene as a Building Block for Conjugated B,N-Chains