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Bismabenzene () is the parent representative of a group of organobismuth compounds that are related to 
An unstable derivative with 4-alkyl substituents was reported in 1982. A stable derivative was reported in 2016. This derivative has two tri(isopropyl)silyl substituents in the ''ortho''-positions and was synthesized from aluminacyclohexadiene, bismuth trichloride, and
benzene
Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, ...
with a carbon
Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent
In chemistry, the valence (US spelling) or valency (British spelling) of an element is the measure of its combining capacity with o ...
atom replaced by a bismuth
Bismuth is a chemical element with the Symbol (chemistry), symbol Bi and atomic number 83. It is a post-transition metal and one of the pnictogens, with chemical properties resembling its lighter group 15 siblings arsenic and antimony. Elemental ...
atom. Bismabenzene itself has been synthesised but not isolated because it is too reactive, tending to instead dimerize
A dimer () ('' di-'', "two" + ''-mer'', "parts") is an oligomer consisting of two monomers joined by bonds that can be either strong or weak, covalent or intermolecular. Dimers also have significant implications in polymer chemistry, inorganic ch ...
in a Diels-Alder addition.
An unstable derivative with 4-alkyl substituents was reported in 1982. A stable derivative was reported in 2016. This derivative has two tri(isopropyl)silyl substituents in the ''ortho''-positions and was synthesized from aluminacyclohexadiene, bismuth trichloride, and DBU
The decibel (symbol: dB) is a relative unit of measurement equal to one tenth of a bel (B). It expresses the ratio of two values of a Power, root-power, and field quantities, power or root-power quantity on a logarithmic scale. Two signals whose ...
.
References
{{reflist, colwidth=30em, refs= {{cite journal , doi = 10.1021/jacs.6b08714, title = An Isolable Bismabenzene: Synthesis, Structure, and Reactivity, year = 2016, last1 = Ishii, first1 = Takuya, last2 = Suzuki, first2 = Katsunori, last3 = Nakamura, first3 = Taichi, last4 = Yamashita, first4 = Makoto, journal = Journal of the American Chemical Society, volume = 138, issue = 39, pages = 12787–12790, pmid = 27654463, url = https://figshare.com/articles/journal_contribution/An_Isolable_Bisma_benzene_Synthesis_Structure_and_Reactivity/3859389 {{cite web , title = Chemists create stable bismuth benzene derivative , author = Fernando Gomollon-Bel , date = September 29, 2016 , url = https://www.chemistryworld.com/news/chemists-create-stable-bismuth-benzene-derivative/1017447.article , publisher = Chemistry World {{cite journal , doi = 10.1021/ja00385a024, title = Stabilization of stibabenzene and bismabenzene by 4-alkyl substituents, year = 1982, last1 = Ashe, first1 = Arthur J., last2 = Diephouse, first2 = Timothy R., last3 = El-Sheikh, first3 = Maher Y., journal = Journal of the American Chemical Society, volume = 104, issue = 21, pages = 5693–5699 {{cite journal , doi = 10.1021/ja00776a063, title = Bismabenzene. Reaction of Group V heteroaromatic compounds with hexafluorobutyne, year = 1972, last1 = Ashe, first1 = Arthur J., last2 = Gordon, first2 = Michael D., journal = Journal of the American Chemical Society, volume = 94, issue = 21, pages = 7596–7597 {{cite journal , last = Ashe , first = A. J. , title = The Group 5 Heterobenzenes , journal = Accounts of Chemical Research , year = 1978 , volume = 11 , issue = 4 , page=156 , doi = 10.1021/ar50124a005 , quote=Bismabenzene is so reactive that is exists in the form of a Diels-Alder dimer (10f) at low temperature (<-10 °C). Organobismuth compounds Bismuth heterocycles Six-membered rings