| Summary: | As with the great progress on the chemistry of benzene (C6H6), “carbon-free” inorganic benzenes have also been explored. However, the isolated examples are limited to the heteroatomic systems (E3E’3 or BP2N3), and other skeletal systems have not been developed. My thesis mainly focused on the synthesis and characterization of neutral and anionic B4N2 benzene analogues with 6π-electron systems by the reduction of 1,4-diaza-2,3,4,5- tetraborinane derivatives bearing a variety of substituents on both boron (B) and nitrogen (N). We isolated neutral and aromatic B4N2 benzene analogue with trimethylphosphine (PMe3) and Chlorine (Cl). By employing the bulky substituents with on B, we successfully synthesized Dewar-type isomer of B4N2 benzene analogue with bridged B−B bond. We also developed the reactivity of strained B atoms towards unsaturated carbon-carbon bonds. Moreover, we explored dianionic B4N2 benzene analogue regards as a zwitterionic inorganic benzene valence isomer. Based on the experimental results, we investigated the aromaticity of neutral and anionic B4N2 benzene analogue by computational studies.
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