Octalene

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For insecticide, see Aldrin.
Octalene
Names
IUPAC name
Octalene
Identifiers
3D model (
JSmol
)
ChEBI
ChemSpider
EC Number
  • 206-215-8
UNII
  • InChI=1S/C14H12/c1-2-6-10-14-12-8-4-3-7-11-13(14)9-5-1/h1-12H/b2-1-,4-3-,5-1-,6-2-,7-3-,8-4-,9-5-,10-6-,11-7-,12-8-,13-9-,13-11-,14-10-,14-12-,14-13-
    Key: OVPVGJFDFSJUIG-VFLSUHNHSA-N
  • InChI=1/C14H12/c1-2-6-10-14-12-8-4-3-7-11-13(14)9-5-1/h1-12H/b2-1-,4-3-,5-1-,6-2-,7-3-,8-4-,9-5-,10-6-,11-7-,12-8-,13-9-,13-11-,14-10-,14-12-,14-13-
    Key: OVPVGJFDFSJUIG-VFLSUHNHBC
  • C1=CC=CC2=C(C=C1)C=CC=CC=C2
Properties
C14H12
Molar mass 180.250 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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Octalene is a polycyclic hydrocarbon composed of two fused cyclooctatetraene rings.[1]

Anions

Octalene can be readily reduced by lithium to a dianion C14H2−12 and, unusually for such a small molecule, a tetraanion C14H4−12.[2] The di-anion has its two negative charges in one ring, converting that ring into a 10-pi electron aromatic system similar to the di-anion of cyclooctatetraene. In the 18-pi electron tetra-anion, both rings effectively have access to 10 pi electrons, leading to a planar, bicyclic aromatic structure analogous to that of naphthalene.

See also

References

  1. doi:10.1021/jo00190a026
    .
  2. ^ Müllen, K., Oth, J. F. M., Engels, H.-W. and Vogel, E. (1979), Dianion and Tetraanion Octalene. Angew. Chem. Int. Ed. Engl., 18: 229–231. doi:10.1002/anie.197902291
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