{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 424762396 | ImageFileL1 = Twistane1.svg | ImageAltL1 = Skeletal formula | ImageFileR1 = Twistane-3D-balls.png | ImageAltR1 = Ball-and-stick model | PIN = Tricyclo[4.4.0.0<sup>3,8</sup>]decane | OtherNames = |Section1={{Chembox Identifiers | Abbreviations = | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 253-14-5
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 4T296B0U5O | CASNo1 = 37165-27-8 | index1_label = (−) | CASNo1_Ref = {{cascite|changed|CAS}} | CASNo2 = 21449-14-9 | index2_label = (+) | CASNo2_Ref = {{cascite|changed|CAS}} | Beilstein = 1919499; 2232311 | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 32904 | ChemSpiderID = 4574225 | ChemSpiderID1 = 34984822 | ChemSpiderID2 = 34984821 | EINECS = | PubChem = 5460768 | SMILES =C1CC2CC3CCC2CC13 | InChI = 1/C10H16/c1-2-8-6-9-3-4-10(8)5-7(1)9/h7-10H,1-6H2 | RTECS = | MeSHName = | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = }} |Section2={{Chembox Properties | C=10|H=16 | Appearance = | Density = | MeltingPtC = 163 to 164.8 | MeltingPt_ref = <ref name="bw"/> | MeltingPt_notes = | BoilingPt = | BoilingPt_notes = | Solubility = | SolubleOther = | Solvent = | pKa = | pKb = }} |Section6={{Chembox Pharmacology | ATCCode_prefix = | ATCCode_suffix = | ATC_Supplemental = }} |Section7={{Chembox Hazards | ExternalSDS = | MainHazards = | NFPA-H = | NFPA-F = | NFPA-R = | NFPA-S = | HPhrases = | PPhrases = | GHS_ref = | FlashPt = | AutoignitionPt = | ExploLimits = | PEL = }} |Section3={{Chembox Structure | Dipole = 0 D | Coordination = D<sub>2</sub> }} }}
'''Twistane''' (IUPAC name: tricyclo[4.4.0.0<sup>3,8</sup>]decane<ref name="asp" />) is an organic compound with the formula C<sub>10</sub>H<sub>16</sub>.<ref name=hopf /> It is a cycloalkane and an isomer of the simplest diamondoid, adamantane, and like adamantane, is not very volatile. Twistane was named for the way its rings are permanently forced into the cyclohexane conformation known as the "twist-boat".<ref name="bw" /> The compound was first reported by Whitlock in 1962.<ref name=whitlock />
==Synthesis== Twistane has been synthesized in a variety of ways. The original 1962 method was based on a bicyclo[2.2.2]octane framework,<ref name=whitlock /> an approach that has seen substantial optimization since.<ref name=Ad>{{cite book|series=Studies in Organic Chemistry|volume=5|title=Adamantane|first=Raymond C.|last=Fort|publisher=Marcel Dekker|location=New York, NY|pp=114-115}}</ref> An alternate approach from 1967 publication relied on an intramolecular aldol condensation of a ''cis''-decalin ketol.<ref name=Deslongchamps /> It is formed when basketane is hydrogenated.<ref name="sym" /> {{dubious|date=January 2015}}
The twistane core also forms from sodium mesitolate and bromoisoprene.<ref name=Ad/>
==Symmetry== The only symmetry operation in twistane is ''rotation'', and there exist three 2-fold axes as shown in the left picture. Thus the point group of twistane is D<sub>2</sub>. Although twistane has four stereocenters, it only exists as two enantiomers. This is because it is symmetric along its C<sub>2</sub> axis.<ref name="ste" />
==Polytwistane== Polytwistane is a hypothetical polymer of fused twistane units awaiting actual synthesis.<ref name=Barua /><ref name=Mayer /><ref name=olbrich /><ref name=Maryasin />
==References== {{Reflist|3|refs= <ref name="asp"> {{Citation | last1 =Quinkert | first1 =Gerhard | author-link = Gerhard Quinkert | last2 =Egert | first2 =Ernst | author2-link = | last3 =Griesinger | first3 =Christian | author3-link = | last4 = trans. Andrew Beard | author4-link = | year = 1996 | title =Aspects of Organic Chemistry: Structure | edition = | volume = | series = | publication-place = Basel, Switzerland | publisher = Helvetica Chimica Acta | pages = 107 | id = | isbn =3-906390-15-2 | doi = | oclc = | url = https://books.google.com/books?id=8k0y-3MY0WgC | accessdate = 2008-12-09 }} </ref> <ref name="bw"> {{Citation | last1 =Beyer | first1 =Hans | author-link = | last2 =Walter | first2 =Wolfgang | author2-link = | last3 = trans. Douglas Lloyd | author3-link = | year = 1997 | title = Organic Chemistry | edition = | volume = | series = | publication-place = | place = | publisher = Horwood Publishing | pages = 416 | id = | isbn = 1-898563-37-3 | doi = | oclc = | url = https://books.google.com/books?id=RXX2RaCplmAC | accessdate = 2008-12-09 }} </ref> <ref name="sym"> {{Citation | last = Ho | first = Tse-Lok | author-link = | year = 1995 | title = Symmetry: A Basis for Synthesis Design | edition = | volume = | series = | publication-place = | place = | publisher = Wiley-IEEE | pages = 69 | id = | isbn = 0-471-57376-0 | doi = | oclc = | url = https://books.google.com/books?id=7kvAOwqRU0sC | accessdate = 2008-12-10 }} </ref> <ref name="ste">
{{Citation | last = Kalsi | first = P. S. | author-link = | year = 2005 | title = Stereochemistry Conformation and Mechanism | edition = | volume = | series = | publication-place = | place = | publisher = New Age Publishers | pages = 94 | id = | isbn = 81-224-1564-4 | doi = | oclc = | url = https://books.google.com/books?id=XLWpHCMP63YC | accessdate = 2008-12-10 }} </ref> <ref name=whitlock>''Tricyclo[4.4.0.03.8]Decane'' H. W. Whitlock Journal of the American Chemical Society 1962 84 (17), 3412-3413 {{doi|10.1021/ja00876a047}}</ref> <ref name=Deslongchamps>''A new synthesis of twistane'' Jean Gauthier, Pierre Deslongchamps Canadian Journal of Chemistry, 1967, 45(3): 297-300, {{doi|10.1139/v67-052}}</ref> <ref name=hopf>''Classics in Hydrocarbon Chemistry: Syntheses, Concepts, Perspectives'' Henning Hopf {{ISBN|978-3-527-29606-4}}. 2000</ref> <ref name=Barua>Barua, S. R., Quanz, H., Olbrich, M., Schreiner, P. R., Trauner, D. and Allen, W. D. (2014), ''Polytwistane''. Chem. Eur. J., 20: 1638–1645. {{doi|10.1002/chem.201303081}}</ref> <ref name=Mayer>''A step toward polytwistane: synthesis and characterization of C2-symmetric tritwistane'' Martin Olbrich, Peter Mayer and Dirk Trauner Org. Biomol. Chem., 2014,12, 108-112 {{doi|10.1039/C3OB42152J}}</ref> <ref name=olbrich>''Synthetic Studies toward Polytwistane Hydrocarbon Nanorods'' Martin Olbrich, Peter Mayer, and Dirk Trauner The Journal of Organic Chemistry Article ASAP 2014 {{doi|10.1021/jo502618g}}</ref> <ref name=Maryasin>''Calculated Nuclear Magnetic Resonance Spectra of Polytwistane and Related Hydrocarbon Nanorods'' Boris Maryasin, Martin Olbrich, Dirk Trauner and Christian Ochsenfeld J. Chem. Theory Comput., 2015,11(3), 1020-1026 {{doi|10.1021/ct5011505}}</ref> }}{{Hydrocarbons}} Category:Polycyclic nonaromatic hydrocarbons Category:Tricyclic compounds