Bismabenzene

Bismabenzene
	source ↗
Names
	Preferred IUPAC name Bismine
	Other names Bismin
Identifiers
CAS Number	289-52-1;
3D model (JSmol)	Interactive image;
ChemSpider	119910;
PubChem CID	136133;
CompTox Dashboard (EPA)	DTXSID50183094;
	InChI InChI=1S/C5H5Bi/c1-2-4-6-5-3-1/h1-5H Key: ZEBPXYQZSWNMLH-UHFFFAOYSA-N;
	SMILES C1=CC=[Bi]C=C1;
Properties
Chemical formula	C5H5Bi
Molar mass	274.075 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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, tending to instead dimerize in a Diels-Alder addition.¹²³

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

An unstable derivative with 4-alkyl substituents was reported in 1982.⁴ A stable derivative, with two ortho tri(isopropyl)silyl substituents, was synthesized from aluminacyclohexadiene, bismuth trichloride, and DBU in 2016.¹⁵

References

Fernando Gomollon-Bel (September 29, 2016). "Chemists create stable bismuth benzene derivative". Chemistry World.
Ashe, Arthur J.; Gordon, Michael D. (1972). "Bismabenzene. Reaction of Group V heteroaromatic compounds with hexafluorobutyne". Journal of the American Chemical Society. 94 (21): 7596–7597. doi:10.1021/ja00776a063.
Ashe, A. J. (1978). "The Group 5 Heterobenzenes". Accounts of Chemical Research. 11 (4): 156. doi:10.1021/ar50124a005. Bismabenzene is so reactive that is exists in the form of a Diels-Alder dimer (10f) at low temperature (<-10 °C).
Ashe, Arthur J.; Diephouse, Timothy R.; El-Sheikh, Maher Y. (1982). "Stabilization of stibabenzene and bismabenzene by 4-alkyl substituents". Journal of the American Chemical Society. 104 (21): 5693–5699. doi:10.1021/ja00385a024.
Ishii, Takuya; Suzuki, Katsunori; Nakamura, Taichi; Yamashita, Makoto (2016). "An Isolable Bismabenzene: Synthesis, Structure, and Reactivity". Journal of the American Chemical Society. 138 (39): 12787–12790. doi:10.1021/jacs.6b08714. PMID 27654463.

[bel-1] Fernando Gomollon-Bel (September 29, 2016). "Chemists create stable bismuth benzene derivative". Chemistry World.

[ashe1972-2] Ashe, Arthur J.; Gordon, Michael D. (1972). "Bismabenzene. Reaction of Group V heteroaromatic compounds with hexafluorobutyne". Journal of the American Chemical Society. 94 (21): 7596–7597. doi:10.1021/ja00776a063.

[AsheDimer-3] Ashe, A. J. (1978). "The Group 5 Heterobenzenes". Accounts of Chemical Research. 11 (4): 156. doi:10.1021/ar50124a005. Bismabenzene is so reactive that is exists in the form of a Diels-Alder dimer (10f) at low temperature (<-10 °C).

[ashe-4] Ashe, Arthur J.; Diephouse, Timothy R.; El-Sheikh, Maher Y. (1982). "Stabilization of stibabenzene and bismabenzene by 4-alkyl substituents". Journal of the American Chemical Society. 104 (21): 5693–5699. doi:10.1021/ja00385a024.

[Ishii-5] Ishii, Takuya; Suzuki, Katsunori; Nakamura, Taichi; Yamashita, Makoto (2016). "An Isolable Bismabenzene: Synthesis, Structure, and Reactivity". Journal of the American Chemical Society. 138 (39): 12787–12790. doi:10.1021/jacs.6b08714. PMID 27654463.

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