Octalene

Octalene is a polycyclic hydrocarbon composed of two fused cyclooctatetraene rings.[1]

Octalene

Names
IUPAC name Octalene
Identifiers
CAS Number	257-55-6
3D model (JSmol)	Interactive image
ChEBI	CHEBI:33084
ChemSpider	119852
EC Number	206-215-8
PubChem CID	136075
InChI 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
SMILES C1=CC=CC2=C(C=C1)C=CC=CC=C2
Properties
Chemical formula	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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Infobox references

Anions

Octalene can be readily reduced by lithium to a di-anion C₁₄H₁₂^2- and, unusually for such a small molecule, a tetra-anion C₁₄H₁₂^4-.[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

• Propalene
• Benzyne
• Pentalene
• Heptalene
• Butalene

References

1. Koseki, S.; Kataoka, M.; Hanamura, M.; Nakajima, T.; Toyota, A. (1984). "Theoretical studies on octalene: the planar and nonplanar structures and the isomerization reactions among the nonplanar structures". The Journal of Organic Chemistry. 49: 2988–2993. 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