Octalene is a polycyclic
hydrocarbon
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic, and their odors are usually weak or ...
composed of two fused
cyclooctatetraene
1,3,5,7-Cyclooctatetraene (COT) is an unsaturated derivative of cyclooctane, with the formula C8H8. It is also known as nnulene. This polyunsaturated hydrocarbon is a colorless to light yellow flammable liquid at room temperature. Because ...
rings.
Anions
Octalene can be readily reduced by lithium to a dianion and, unusually for such a small molecule, a tetraanion .
[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
1,3,5,7-Cyclooctatetraene (COT) is an unsaturated derivative of cyclooctane, with the formula C8H8. It is also known as nnulene. This polyunsaturated hydrocarbon is a colorless to light yellow flammable liquid at room temperature. Because ...
. 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
Naphthalene is an organic compound with formula . It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromat ...
.
See also
*
Propalene
Propalene or bicyclo .1.0uta-1,3-diene is a polycyclic hydrocarbon composed of two fused cyclopropene rings. Computational studies indicate that the molecule is planar, with the carbon framework forming a parallelogram that has distinctly alter ...
*
Benzyne
*
Pentalene
Pentalene is a polycyclic hydrocarbon composed of two fused cyclopentadiene rings. It has chemical formula . It is antiaromatic, because it has 4''n'' π electrons where ''n'' is any integer. For this reason it dimerizes even at temperatures as ...
*
Heptalene
*
Butalene
Butalene is a polycyclic hydrocarbon composed of two fused cyclobutadiene rings. A reported possible synthesis of it involves an elimination reaction from a Dewar benzene derivative. The structure itself can be envisioned as benzene with an inter ...
References
{{reflist
Polycyclic nonaromatic hydrocarbons
Bicyclic compounds