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Swager, T. M.; Dougherty, D. A.; Grubbs, R. H. (1988). "Strained rings as a source of unsaturation: polybenzvalene, a new soluble polyacetylene precursor".
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371:) 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
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present in benzvalene, the pure compound (~71 kcal/mol higher in energy than benzene) easily detonates, for example by scratching.
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Kaplan, Louis; Wilzbach, K. E. (1968-06-01). "Photolysis of benzene vapor. Benzvalene formation at wavelengths 2537-2370 A".
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Scott, Lawrence T.; Jones, Maitland. (1972). "Rearrangements and interconversions of compounds of the formula (CH)n".
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Wilzbach, K. E.; Ritscher, J. S.; Kaplan, L. (1967). "Benzvalene, the
Tricyclic Valence Isomer of Benzene".
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to 1,3-dienes and for this reason polybenzvalene has been investigated as a precursor to
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Katz, T. J.; Roth, R. J.; Acton, N.; Carnahan, E. J. (1999). "Synthesis of
Benzvalene".
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Christl, M. (1981). "Benzvalene—Properties and
Synthetic Potential".
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Katz, T. J.; Wang, E. J.; Acton, N. (1971). "Benzvalene synthesis".
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Except where otherwise noted, data are given for materials in their
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rings which again makes it a sensitive material. The rings can be
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332:. It was first synthesized in 1967 by K. E. Wilzbach et al. via
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at −45 °C. It can also be formed in low yield (along with
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and the synthesis was later improved by Thomas J. Katz et al.
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441:Angewandte Chemie International Edition in English
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386:transition is believed to take place through a
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410:. This polymer contains highly strained
343:The 1971 synthesis consisted of treating
615:Journal of the American Chemical Society
553:Journal of the American Chemical Society
498:Journal of the American Chemical Society
469:Journal of the American Chemical Society
378:The compound converts to benzene with a
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190:InChI=1S/C6H6/c1-2-4-5-3(1)6(4)5/h1-6H
200:InChI=1/C6H6/c1-2-4-5-3(1)6(4)5/h1-6H
193:Key: VMQPMGHYRISRHO-UHFFFAOYSA-N
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203:Key: VMQPMGHYRISRHO-UHFFFAOYAJ
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684:Substances discovered in the 1970s
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382:of approximately 10 days. This
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359:and methyllithium in
37:Preferred IUPAC name
674:Tricyclic compounds
664:Explosive chemicals
627:10.1021/ja00217a049
600:10.1021/cr60276a004
565:10.1021/ja01014a086
511:10.1021/ja00744a045
482:10.1021/ja00980a053
324:and one of several
269: g·mol
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398:Benzvalene can be
384:symmetry-forbidden
380:chemical half-life
306:Infobox references
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647:Media related to
559:(12): 3291–3292.
538:10.1021/jo990883g
314:Chemical compound
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146:CompTox Dashboard
89:Interactive image
41:Tricyclohex-3-ene
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48:Identifiers
621:(9): 2973.
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406:process to
400:polymerized
233:Properties
17:Benzvalene
658:Categories
649:Benzvalene
594:(2): 181.
426:References
416:isomerized
334:photolysis
318:Benzvalene
262:Molar mass
100:ChemSpider
76:3D model (
55:CAS Number
573:0002-7863
388:diradical
65:659-85-8
365:fulvene
338:benzene
330:benzene
326:isomers
299:what is
297: (
121:PubChem
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320:is an
294:verify
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267:78.114
217:SMILES
134:136470
109:120239
31:Names
402:in a
347:with
182:InChI
78:JSmol
569:ISSN
404:ROMP
367:and
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