3D model (JSmol)
CompTox Dashboard (EPA)
|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).
|what is ?)(|
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. 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.
Benzvalene can be polymerized in a ROMP process to polybenzvalene. 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.
- Christl, M. (1981). "Benzvalene—Properties and Synthetic Potential". Angewandte Chemie International Edition in English. 20 (67): 529–546. doi:10.1002/anie.198105291.
- Katz, T. J.; Wang, E. J.; Acton, N. (1971). "Benzvalene synthesis". Journal of the American Chemical Society. 93 (15): 3782. doi:10.1021/ja00744a045.
- Katz, T. J.; Roth, R. J.; Acton, N.; Carnahan, E. J. (1999). "Synthesis of Benzvalene". The Journal of Organic Chemistry. 64 (20): 7663. doi:10.1021/jo990883g.
- Kaplan, Louis; Wilzbach, K. E. (1968-06-01). "Photolysis of benzene vapor. Benzvalene formation at wavelengths 2537-2370 A". Journal of the American Chemical Society. 90 (12): 3291–3292. doi:10.1021/ja01014a086. ISSN 0002-7863.
- Scott, Lawrence T.; Jones, Maitland. (1972). "Rearrangements and interconversions of compounds of the formula (CH)n". Chemical Reviews. 72 (2): 181. doi:10.1021/cr60276a004.
- Swager, T. M.; Dougherty, D. A.; Grubbs, R. H. (1988). "Strained rings as a source of unsaturation: polybenzvalene, a new soluble polyacetylene precursor". Journal of the American Chemical Society. 110 (9): 2973. doi:10.1021/ja00217a049.
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