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.

trans-Bicalicene

Names
IUPAC names (4aZ,8aZ)-Dicyclopenta[a,e]dicyclopropa[c,g][8]annulene Dicyclopenta[a,e]dicyclopropa[c,g]cyclooctene
Identifiers
CAS Number	73091-52-8
3D model (JSmol)	Interactive image
ChemSpider	4423214
PubChem CID	5257656
InChI InChI=1S/C16H8/c1-3-9-10(4-1)14-8-16(14)12-6-2-5-11(12)15-7-13(9)15/h1-8H/b13-9-,14-10-,15-11-,16-12- Key: FVDGMBFXSFSQOU-NONDJZLBSA-N InChI=1/C16H8/c1-3-9-10(4-1)14-8-16(14)12-6-2-5-11(12)15-7-13(9)15/h1-8H/b13-9-,14-10-,15-11-,16-12- Key: FVDGMBFXSFSQOU-NONDJZLBBM
SMILES C1=CC2=C3C=C3C4=CC=CC4=C5C=C5C2=C1
Properties
Chemical formula	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

Names
IUPAC name Dicyclopenta[a,c]dicyclopropa[e,g]cyclooctene
Identifiers
CAS Number	122605-73-6
3D model (JSmol)	Interactive image
PubChem CID	101619525
InChI InChI=1S/C16H8/c1-3-9-10-4-2-6-12(10)14-8-16(14)15-7-13(15)11(9)5-1/h1-8H Key: MIGVZWUAYKWALJ-UHFFFAOYSA-N
SMILES C1=CC2=C3C=C3C4=CC4=C5C=CC=C5C2=C1
Properties
Chemical formula	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

• Calicene

References

1. 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.
2. 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.
3. 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.