Bicalicene

trans-Bicalicene
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
UNII
  • 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
  • C1=CC2=C3C=C3C4=CC=CC4=C5C=C5C2=C1
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).
cis-Bicalicene
Names
IUPAC name
Dicyclopenta[a,c]dicyclopropa[e,g]cyclooctene
Identifiers
3D model (JSmol)
  • 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
  • C1=CC2=C3C=C3C4=CC4=C5C=CC=C5C2=C1
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).

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.

  1. ^ a b Yonedo S, Shibata M, Kida S, Yoshida Zi, 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.