Bicalicene

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trans-Bicalicene
Trans-Bicalicene.svg
Names
IUPAC names
(4aZ,8aZ)-Dicyclopenta[a,e]dicyclopropa[c,g][8]annulene
Dicyclopenta[a,e]dicyclopropa[c,g]cyclooctene
Identifiers
3D model (JSmol)
ChemSpider
Properties
C16H8
Molar mass 200.240 g·mol−1
Melting point 125-130°C (dec)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
cis-Bicalicene
Cis-Bicalicene.svg
Names
IUPAC name
Dicyclopenta[a,c]dicyclopropa[e,g]cyclooctene
Identifiers
3D model (JSmol)
Properties
C16H8
Molar mass 200.240 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

Bicalicene is polycyclic hydrocarbon with chemical formula C16H8, composed of linked two cyclopentadiene ring and two cyclopropene ring.[1] There are two isomers: cis-bicalicene and trans-bicalicene.

Synthesis[edit]

Bicalicene is prepared by treatment of 1,2-bis(tert-butylthio)-3,3-dichlorocyclopropene with cyclopentadiene anion, followed by desulfurizing stannylation with tributyltin hydride and silica gel.[1]

Properties[edit]

trans-Bicalicene is polycyclic aromatic hydrocarbon with 16 pi electrons due to positive charge on the carbon atom of triangular ring and a negative charge on the carbon atom of pentagonal ring.[2]

cis-Bicalicene is an antiaromatic hydrocarbon.[3]

See also[edit]

References[edit]

  1. ^ a b c Yonedo S, Shibata M, Kida S, Yoshida Z, Kai Y, Miki K, Kasai N (January 1984). "A Novel Aromatic Hydrocarbon with 16π-Electron Periphery:"Cyclic Bicalicene"". Angewandte Chemie International Edition in English. 23 (1): 63–64. doi:10.1002/anie.198400631.
  2. ^ Oziminski WP, Palusia M (2013). "Capturing the elusive aromaticity of bicalicene". Physical Chemistry Chemical Physics. 15: 3286–3293. doi:10.1039/C2CP43426A.
  3. ^ Jelena Đurđević Nikolić; Ivan Gutman (2016). "A Comparative Study of the Two Isomers of Bicalicene". Polycyclic Aromatic Compounds: 1–7. doi:10.1080/10406638.2016.1140659.