octalene
{{For|insecticide|Aldrin}}
{{chembox
| ImageFile = Octalene.svg
| ImageSize = 200px
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid =
| IUPACName = Octalene
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 257-55-6
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = X4JL62R2HN
| PubChem = 136075
| EINECS = 206-215-8
| ChEBI = 33084
| ChemSpiderID = 119852
| SMILES = C1=CC=CC2=C(C=C1)C=CC=CC=C2
| 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-
| InChIKey = OVPVGJFDFSJUIG-VFLSUHNHBC
| StdInChI = 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-
| StdInChIKey = OVPVGJFDFSJUIG-VFLSUHNHSA-N
}}
|Section2={{Chembox Properties
| C=14|H=12
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
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|Section7={{Chembox Hazards
| MainHazards =
| FlashPt =
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Octalene is a polycyclic hydrocarbon composed of two fused cyclooctatetraene rings.{{cite journal|doi=10.1021/jo00190a026 | volume=49 | title=Theoretical studies on octalene: the planar and nonplanar structures and the isomerization reactions among the nonplanar structures | year=1984 | journal=The Journal of Organic Chemistry | pages=2988–2993 | last1 = Koseki | first1 = S. | last2 = Kataoka | first2 = M. | last3 = Hanamura | first3 = M. | last4 = Nakajima | first4 = T. | last5 = Toyota | first5 = A.| issue=16 }}
Anions
Octalene can be readily reduced by lithium to a dianion {{chem2|C14H12(2-)}} and, unusually for such a small molecule, a tetraanion {{chem2|C14H12(4-)}}.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 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.