Bicalicene
Bicalicene is polycyclic hydrocarbon with chemical formula C16H8, composed of two cyclopentadiene and two cyclopropene rings linked into a larger eight-membered ring.[1] There are two isomers: cis-bicalicene and trans-bicalicene. It is a dimer of calicene.
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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). | |
| Infobox references | |
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| Names | |
|---|---|
| IUPAC name
Dicyclopenta[a,c]dicyclopropa[e,g]cyclooctene | |
| Identifiers | |
3D model (JSmol) |
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PubChem CID |
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| 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 | |
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
- Yonedo S, Shibata M, Kida S, Yoshida Z, Kai Y, Miki K, Kasai N (January 1984). "A Novel Aromatic Hydrocarbon with 16 π-Electron Periphery: "Cyclic Bicalicene"". Angewandte Chemie International Edition in English. 23 (1): 63–64. doi:10.1002/anie.198400631.
- Oziminski WP, Palusia M (2013). "Capturing the elusive aromaticity of bicalicene". Physical Chemistry Chemical Physics. 15 (9): 3286–3293. Bibcode:2013PCCP...15.3286O. doi:10.1039/C2CP43426A.
- Jelena Đurđević Nikolić; Ivan Gutman (2016). "A Comparative Study of the Two Isomers of Bicalicene". Polycyclic Aromatic Compounds. 38: 1–7. doi:10.1080/10406638.2016.1140659. S2CID 99213944.
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