270:
37:
28:
420:
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306:
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Twistane has been synthesized in a variety of ways. The original 1962 method was based on a bicyclooctane framework. A 1967 publication concerned an
671:
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Boris
Maryasin, Martin Olbrich, Dirk Trauner and Christian Ochsenfeld J. Chem. Theory Comput., 2015,11(3), 1020-1026
460:
500:
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380:
546:, and there exist three 2-fold axes as shown in the left picture. Thus the point group of twistane is D
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Martin
Olbrich, Peter Mayer, and Dirk Trauner The Journal of Organic Chemistry Article ASAP 2014
559:
515:
135:
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Calculated
Nuclear Magnetic Resonance Spectra of Polytwistane and Related Hydrocarbon Nanorods
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Jean
Gauthier, Pierre Deslongchamps Canadian Journal of Chemistry, 1967, 45(3): 297-300,
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Martin
Olbrich, Peter Mayer and Dirk Trauner Org. Biomol. Chem., 2014,12, 108-112
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A step toward polytwistane: synthesis and characterization of C2-symmetric tritwistane
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H. W. Whitlock
Journal of the American Chemical Society 1962 84 (17), 3412-3413
503:
known as the "twist-boat". The compound was first reported by
Whitlock in 1962.
480:
36:
555:
492:
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351:
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801:
499:. Twistane was named for the way its rings are permanently forced into the
473:
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820:
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203:
858:
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527:
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163 to 164.8 °C (325.4 to 328.6 °F; 436.1 to 437.9 K)
713:
664:
Classics in
Hydrocarbon Chemistry: Syntheses, Concepts, Perspectives
410:
Except where otherwise noted, data are given for materials in their
27:
632:; Egert, Ernst; Griesinger, Christian; trans. Andrew Beard (1996),
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402:
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597:
Beyer, Hans; Walter, Wolfgang; trans. Douglas Lloyd (1997),
253:
35:
26:
638:, Basel, Switzerland: Helvetica Chimica Acta, p. 107,
832:
Synthetic
Studies toward Polytwistane Hydrocarbon Nanorods
788:
Barua, S. R., Quanz, H., Olbrich, M., Schreiner, P. R.,
428:
293:
InChI=1/C10H16/c1-2-8-6-9-3-4-10(8)5-7(1)9/h7-10H,1-6H2
578:of fused twistane units awaiting actual synthesis.
215:
98:
90:
82:
8:
542:The only symmetry operation in twistane is
760:Stereochemistry Conformation and Mechanism
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680:
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15:
235:
635:Aspects of Organic Chemistry: Structure
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311:
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728:Symmetry: A Basis for Synthesis Design
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7:
592:
590:
876:Polycyclic nonaromatic hydrocarbons
603:, Horwood Publishing, p. 416,
495:, and like adamantane, is not very
206:
763:, New Age Publishers, p. 94,
14:
796:. Chem. Eur. J., 20: 1638–1645.
418:
341:
574:Polytwistane is a hypothetical
414:(at 25 °C , 100 kPa).
335:
1:
550:. Although twistane has four
459:name: tricyclodecane) is an
706:A new synthesis of twistane
22:
897:
731:, Wiley-IEEE, p. 69,
792:and Allen, W. D. (2014),
408:
373:
322:
302:
280:
66:
54:
49:
21:
558:. This is because it is
554:, it only exists as two
501:cyclohexane conformation
802:10.1002/chem.201303081
40:
31:
757:Kalsi, P. S. (2005),
560:symmetric along its C
381:Coordination geometry
39:
30:
725:Ho, Tse-Lok (1995),
530:. It is formed when
56:Preferred IUPAC name
881:Tricyclic compounds
695:10.1021/ja00876a047
359: g·mol
136:Beilstein Reference
18:
821:10.1039/C3OB42152J
534:is hydrogenated.
516:aldol condensation
441:Infobox references
41:
32:
16:
859:10.1021/ct5011505
840:10.1021/jo502618g
672:978-3-527-29606-4
630:Quinkert, Gerhard
600:Organic Chemistry
449:Chemical compound
447:
446:
249:CompTox Dashboard
141:1919499; 2232311
124:Interactive image
45:
44:
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619:
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487:of the simplest
461:organic compound
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425:
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358:
343:
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330:Chemical formula
314:C1CC2CC3CCC2CC13
273:
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181:(−):
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714:10.1139/v67-052
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436: ?)
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687:TricycloDecane
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513:intramolecular
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412:standard state
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266:DTXSID20420120
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60:Tricyclodecane
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2:
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770:81-224-1564-4
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738:0-471-57376-0
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677:
673:
669:
666:Henning Hopf
665:
660:
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647:
645:3-906390-15-2
641:
637:
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625:
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612:
610:1-898563-37-3
606:
602:
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593:
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569:
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557:
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552:stereocenters
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396:Dipole moment
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365:Melting point
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794:Polytwistane
793:
784:
774:, retrieved
759:
752:
742:, retrieved
727:
720:
705:
701:
686:
663:
659:
649:, retrieved
634:
624:
614:, retrieved
599:
573:
570:Polytwistane
543:
541:
519:
510:
452:
451:
67:Identifiers
790:Trauner, D.
556:enantiomers
481:cycloalkane
323:Properties
156:CHEBI:32904
870:Categories
776:2008-12-10
744:2008-12-10
651:2008-12-09
616:2008-12-09
582:References
493:adamantane
489:diamondoid
479:. It is a
374:Structure
352:Molar mass
237:4T296B0U5O
189:(+):
167:ChemSpider
111:3D model (
100:21449-14-9
97:(+):
92:37165-27-8
74:CAS Number
532:basketane
507:Synthesis
463:with the
17:Twistane
544:rotation
538:Symmetry
497:volatile
453:Twistane
192:34984821
184:34984822
84:253-14-5
576:polymer
524:decalin
483:and an
465:formula
434:what is
432: (
357:136.238
217:5460768
204:PubChem
176:4574225
767:
735:
674:. 2000
670:
642:
607:
528:ketone
485:isomer
429:verify
426:
307:SMILES
50:Names
518:of a
457:IUPAC
285:InChI
147:ChEBI
113:JSmol
765:ISBN
733:ISBN
668:ISBN
640:ISBN
605:ISBN
564:axis
228:UNII
855:doi
836:doi
817:doi
798:doi
710:doi
691:doi
520:cis
254:EPA
207:CID
872::
679:^
589:^
566:.
526:di
491:,
477:16
471:10
401:0
345:16
339:10
857::
838::
819::
800::
712::
693::
562:2
548:2
522:-
474:H
468:C
455:(
424:N
403:D
388:2
386:D
342:H
336:C
256:)
252:(
115:)
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