Benzvalene
Chemical compound / From Wikipedia, the free encyclopedia
Benzvalene is an organic compound and one of several isomers of benzene.[1] It was first synthesized in 1967 by K. E. Wilzbach et al. [2] via photolysis of benzene and the synthesis was later improved by Thomas J. Katz et al.[3][4]
Names | |
---|---|
Preferred IUPAC name
Tricyclo[3.1.0.02,6]hex-3-ene | |
Identifiers | |
| |
3D model (JSmol) |
|
ChemSpider |
|
PubChem CID |
|
CompTox Dashboard (EPA) |
|
| |
| |
Properties | |
C6H6 | |
Molar mass | 78.114 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
The 1971 synthesis consisted of treating cyclopentadiene with methyllithium in dimethyl ether and then with dichloromethane and methyllithium in diethyl ether at −45 °C. It can also be formed in low yield (along with fulvene and Dewar benzene) by irradiation of benzene at 237 to 254 nm.[5] The hydrocarbon in solution was described as having an extremely foul odor. Due to the high steric strain present in benzvalene, the pure compound (~71 kcal/mol higher in energy than benzene) easily detonates, for example by scratching.
The compound converts to benzene with a chemical half-life of approximately 10 days. This symmetry-forbidden transition is believed to take place through a diradical intermediate.[6]