Bismole

Not to be confused with Bismoll or Pepto-Bismol.
Bismole
Skeletal formula of bismole
Ball-and-stick model of the bismole molecule
Names
IUPAC name
1H-Bismole
Identifiers
89067-15-2 YesY
ChemSpider 24751865 YesY
Jmol 3D model Interactive image
Properties
C4H5Bi
Molar mass 262.06 g·mol−1
Related compounds
Related compounds
Pyrrole, phosphole, arsole, stibole
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Bismole is a theoretical heterocyclic organic compound, a five-membered ring with the formula C4H4BiH. It is classified as a metallole. It can be viewed as an structural analog of pyrrole, with bismuth replacing the nitrogen atom of pyrrole. The unsubstituted compound has not been isolated due to the high energy of the Bi-H bond. Substituted derivatives, which have been synthesized, are called bismoles.[1]

Reactions

2,5-Bis(trimethylsilyl)-3,4-dimethyl-1-phenyl-1H-bismole, for example, can be formed by the reaction of (1Z,3Z)-1,4-bis(trimethylsilyl)-1,4-diiodobuta-2,3-dimethyl-1,3-diene and diiodophenylbismuthine. Bismoles can be used to form ferrocene-like sandwich compounds.[2]

See also

References

  1. Suzuki, Hitomi; Komatsu, Naoki; Ogawa, Takuji; Murafuji, Toshihiro; Ikegami, Tohru; Matano, Yoshihiro (2001), "4: Bismuth-Containing Heterocycle", Organobismuth Chemistry, Elsevier, pp. 329–344, ISBN 978-0-444-20528-5
  2. Katritzky, Alan R.; Kirby, Gordon W.; Meth-Cohn, Otto; Rees, Charles W., eds. (1995), Synthesis: Carbon with Two Heteroatoms, Each Attached by a Single Bond, Volume 4 of Comprehensive Organic Functional Group Transformations, Elsevier, pp. 1038–1040, ISBN 978-0-08-042325-8
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