Bicalicene
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| Names | |
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| IUPAC names
(4aZ,8aZ)-Dicyclopenta[a,e]dicyclopropa[c,g][8]annulene
Dicyclopenta[a,e]dicyclopropa[c,g]cyclooctene | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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| 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).
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| |
| 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).
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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
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
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
References
- ^ a b c Yonedo, Shigeo; Shibata, Mitsuhiro; Kida, Shuji; Yoshida, Zen-ichi; Kai, Yasusi; Miki, Kunio; Kasai, Nobutami (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.
{{cite journal}}: Unknown parameter|name-list-format=ignored (|name-list-style=suggested) (help) - ^ Oziminski WP, Palusia M (2013). "Capturing the elusive aromaticity of bicalicene". Physical Chemistry Chemical Physics. 15: 3286–3293. doi:10.1039/C2CP43426A.
- ^ 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.