Benzvalene
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| IUPAC name
tricyclo[3.1.0.02,6]hex-3-ene
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| ChemSpider | 120239 |
| Jmol 3D model | Interactive image |
| PubChem | 136470 |
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| C6H6 | |
| Molar mass | 78.11 g·mol−1 |
| Vapor pressure | {{{value}}} |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Benzvalene is an organic compound and one of several isomers of benzene.[1] It was synthesised in 1971 by Thomas J. Katz et al.[2][3]
The 1971 synthesis consisted of treating cyclopentadiene with methyllithium in dimethyl ether and then with dichloromethane and methyllithium in diethyl ether at -45°C. The hydrocarbon in solution was described as having an extraordinary mephitic odor. Due to the high steric strain present in benzvalene, the pure compound 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.[4]
Polybenzvalene
Benzvalene can be polymerized in a ROMP process to polybenzvalene.[5] This polymer contains highly strained bicyclobutane rings which again makes it a sensitive material. The rings can be isomerized to 1,3-dienes and for this reason polybenzvalene has been investigated as a precursor to polyacetylene.
References
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Rearrangements and interconversions of compounds of the formula (CH)n Lawrence T. Scott, Maitland. Jones Chem. Rev., 1972, 72 (2), pp 181–202 doi:10.1021/cr60276a004
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
External link
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