Bismabenzene

Bismabenzene (C5H5Bi) is the parent representative of a group of organobismuth compounds that are related to benzene with a carbon atom replaced by a bismuth atom. Bismabenzene itself has been synthesised but not isolated because it is too reactive.[1][2]

Bond lengths and angles of benzene, pyridine, phosphorine, arsabenzene, stibabenzene, and bismabenzene

An unstable derivative with 4-alkyl substituents was reported in 1982.[3] A stable derivative was reported in 2016.[1][4] This derivative has two tri(isopropyl)silyl substituents in the ortho positions and was synthesised from aluminacyclohexadiene, bismuth trichloride and DBU.

References
  1. Chemists create stable bismuth benzene derivative Fernando Gomollon-Bel By Fernando Gomollon-Bel 29 September 2016 https://www.chemistryworld.com/news/chemists-create-stable-bismuth-benzene-derivative/1017447.article
  2. Bismabenzene. Reaction of Group V heteroaromatic compounds with hexafluorobutyne Arthur J. Ashe III and Michael D. Gordon Journal of the American Chemical Society 1972 94 (21), 7596-7597 doi: 10.1021/ja00776a063
  3. Stabilization of stibabenzene and bismabenzene by 4-alkyl substituents Arthur J. Ashe III, Timothy R. Diephouse, and Maher Y. El-Sheikh Journal of the American Chemical Society 1982 104 (21), 5693-5699 {{DOI: 10.1021/ja00385a024}}
  4. An Isolable Bismabenzene: Synthesis, Structure, and Reactivity Takuya Ishii, Katsunori Suzuki, Taichi Nakamura, and Makoto Yamashita Journal of the American Chemical Society Article 2016 ASAP doi: 10.1021/jacs.6b08714
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