Bicalicene

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 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 c1c/c/2c\3/c(c3)c4/c(c/5\c(c2c1)c5)/ccc4
Properties
Chemical formula	C16H8
Molar mass	200.24 g·mol−1
Melting point	125-130°C (dec)
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
SMILES C1=CC2=C3C=C3C4=CC4=C5C=CC=C5C2=C1
Properties
Chemical formula	C16H8
Molar mass	200.24 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.

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.

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.

cis-bicalicene is an antiaromatic hydrocarbon.