562:
232:
139:
400:
405:
24:
481:
593:. However, the absorption edge of light does not extend past 300 nm whereas most solar radiation has wavelengths longer than 400 nm. Quadricyclane's relative stability and high energy content have also given rise to its use as a propellant additive or fuel. However, quadricyclane undergoes
413:
380:
727:
Philippopoulos, Constantine; Economou, Dimitrios; Economou, Constantine; Marangozis, John (1983). "Norbornadiene-quadricyclane system in the photochemical conversion and storage of solar energy".
494:
597:
at relatively low temperatures (less than 400 °C). This property limits its applications, as propulsion systems may operate at temperatures exceeding 500 °C.
281:
532:
of quadricyclane proceeds slowly at low temperatures. Because of quadricyclane's strained structure and thermal stability, it has been studied extensively.
451:
698:
556:, etc., may be used but with a lesser yield. The yield is higher for freshly distilled norbornadiene, but commercial reagents will suffice.
609:
to give a mixture of nortricyclyl acetate and exo-norbornyl acetate. Quadricyclane also reacts with many dienophiles to form 1:1 adducts.
713:
Dubonosov, A. D; Bren, V. A; Chernoivanov, V. A. “Norbornadiene – quadricyclane as an abiotic system for the storage of solar energy.”
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Striebich, R; Lawrence, J (2003). "Thermal decomposition of high-energy density materials at high pressure and temperature".
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445:
189:
561:
210:
146:
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134:
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Quadricyclane is produced by the irradiation of norbornadiene (bicyclohepta-2,5-diene) in the presence of
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Industrial & Engineering
Chemistry Product Research and Development
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Petrov, V. A; Vasil’ev, N. V. “Synthetic
Chemistry of Quadricyclane.”
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Except where otherwise noted, data are given for materials in their
95:
85:
255:
InChI=1S/C7H8/c1-2-4-5(2)7-3(1)6(4)7/h2-7H,1H2/t2-,3+,4+,5-,6+,7-
437:
265:
InChI=1/C7H8/c1-2-4-5(2)7-3(1)6(4)7/h2-7H,1H2/t2-,3+,4+,5-,6+,7-
671:
Cahill, P; Steppel, R. Process of quadricyclane production.
215:
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is a strained, multi-cyclic hydrocarbon with the formula CH
589:= −89 kJ/mol). This reaction has been proposed to store
489:
544:
or ethyl
Michler's ketone. Other sensitizers, such as
358:
108 °C (226 °F; 381 K) at 987 hPa
677:
filed
September 12, 2003, and issued March 18, 2004
524:. A white volatile colorless liquid, it is highly
577:into quadricyclane is achieved with ~300 nm
177:
71:
647:Smith, Claiborune D. (1971). "Quadricyclane".
8:
756:Journal of Analytical and Applied Pyrolysis
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585:energy is liberated in the form of heat (
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581:. When converted back to norbornadiene,
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693:. New Age International. p. 366.
690:Organic Reactions And Their Mechanisms
348:−44 °C (−47 °F; 229 K)
128:
569:Proposed applications to solar energy
258:Key: DGZUEIPKRRSMGK-BEOVHNCFSA-N
50:quadricycloheptane, tetracycloheptane
7:
268:Key: DGZUEIPKRRSMGK-BEOVHNCFBK
168:
605:Quadricyclane readily reacts with
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475:(at 25 °C , 100 kPa).
1:
768:10.1016/S0165-2370(02)00181-X
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528:molecule (78.7 kcal/mol).
630:Current Organic Synthesis
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328:92.14 g/mol
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35:
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21:
715:Russian Chemical Reviews
659:10.15227/orgsyn.051.0133
446:Precautionary statements
674:U.S. patent 10,661,194
798:Tetracyclic compounds
595:thermal decomposition
37:Preferred IUPAC name
741:10.1021/i300012a021
687:Kalsi, P S (2000).
365:Solubility in water
18:
717:71 (2002): 917–927
573:The conversion of
502:Infobox references
16:
700:978-81-224-1268-0
650:Organic Syntheses
632:3 (2006): 215–259
510:Chemical compound
508:
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428:Hazard statements
211:CompTox Dashboard
97:Interactive image
41:Tetracycloheptane
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542:Michler's ketone
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305:Chemical formula
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289:C1C2C3C2C4C1C34
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17:Quadricyclane
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793:Cyclopropanes
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575:norbornadiene
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530:Isomerization
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514:Quadricyclane
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129:ECHA InfoCard
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788:Hydrocarbons
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689:
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591:solar energy
586:
579:UV radiation
572:
554:acetophenone
550:benzophenone
539:
513:
512:
419:
381:
56:Identifiers
48:Other names
607:acetic acid
583:ring strain
536:Preparation
414:Signal word
338:0.982 g/cm
298:Properties
135:100.005.450
782:Categories
762:(2): 339.
735:(4): 627.
393:Pictograms
370:Insoluble
324:Molar mass
199:8E0K9BG24C
108:ChemSpider
84:3D model (
63:CAS Number
601:Reactions
384:labelling
156:205-994-1
148:EC Number
526:strained
375:Hazards
117:30796462
73:278-06-8
546:acetone
495:what is
493: (
334:Density
318:
166:PubChem
697:
490:verify
487:
420:Danger
282:SMILES
31:Names
613:Notes
247:InChI
179:78961
86:JSmol
695:ISBN
520:(CH)
464:P310
460:P284
456:P260
452:P210
438:H330
434:H226
190:UNII
764:doi
737:doi
655:doi
382:GHS
216:EPA
169:CID
784::
760:70
758:.
733:22
731:.
653:.
637:^
621:^
587:ΔH
552:,
548:,
462:,
458:,
454:,
436:,
386::
770:.
766::
743:.
739::
703:.
662:.
657::
522:6
518:2
485:N
316:8
314:H
312:7
310:C
218:)
214:(
88:)
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