title: An Isolable Bismabenzene: Synthesis, Structure, and Reactivity.
abstract: A stable bismabenzene was synthesized, isolated, and structurally characterized. The prospective aromaticity of this heavy benzene, bearing a sixth-row element, was examined by X-ray crystallography and NMR and UV-vis spectroscopy, as well as theoretical DFT calculations. Structural analysis of this bismabenzene revealed a planar ring containing unsaturated Bi-C and C-C bonds. As bond alternations could not be observed, these results are consistent with the formal criteria of aromaticity. Theoretical calculations also support the aromatic nature of this bismabenzene, which reacted with an alkyne to form the corresponding [4+2] cycloadduct, thus demonstrating a small yet tangible aromatic stabilization energy.
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University , 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan.
authors.forename: Takuya
authors.initials: T
authors.lastname: Ishii
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University , 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan.
authors.forename: Katsunori
authors.initials: K
authors.lastname: Suzuki
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University , 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan.
authors.forename: Taichi
authors.initials: T
authors.lastname: Nakamura
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University , 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan.
authors.forename: Makoto
authors.initials: M
authors.lastname: Yamashita