Cuneane

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Saturated hydrocarbon compound (C8H8)

title: "Cuneane" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["polycyclic-nonaromatic-hydrocarbons", "cyclopropanes", "cyclobutanes"] description: "Saturated hydrocarbon compound (C8H8)" topic_path: "general/polycyclic-nonaromatic-hydrocarbons" source: "https://en.wikipedia.org/wiki/Cuneane" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Saturated hydrocarbon compound (C8H8) ::

| ImageFile = Cuneane-HF-Mercury-3D-balls.png | ImageFile_Ref = | ImageSize = 160 | ImageName = Ball and stick model of cuneane (1R,2R,3S,4S,5S,6R,7R,8S) | PIN = Pentacyclo[3.3.0.02,4.03,7.06,8]octane |Section1={{Chembox Identifiers | CASNo = 20656-23-9 | CASNo_Ref = | PubChem = 140734 | ChemSpiderID = 124127 | ChemSpiderID_Ref = | SMILES = C12C3C4C3C5C1C2C45 | StdInChI = 1S/C8H8/c1-2-5(1)6-3-4(6)8(2)7(1)3/h1-8H | StdInChI_Ref = | StdInChIKey = YIJMEXRVJPVGIY-UHFFFAOYSA-N | StdInChIKey_Ref = |Section2={{Chembox Properties | C=8 | H=8 | Density = 1.578 g/ml

Cuneane ({{cite journal |author1=R. Criegee |author2=R. Askani | title = Octamethylsemibullvalene | journal = Angewandte Chemie International Edition in English | volume = 7 | issue = 7 | year = 1968 | pages = 537 | doi = 10.1002/anie.196805371}}) is a saturated hydrocarbon with the formula and a 3D structure resembling a wedge, hence the name. Cuneane may be produced from cubane by metal-ion-catalyzed σ-bond rearrangement.{{cite book |author1=Michael B. Smith |author2=Jerry March | title =March's Advanced Organic Chemistry | edition = 5th | publisher = John Wiley & Sons, Inc. | year = 2001 | pages = 1459 | isbn = 0-471-58589-0}}{{cite journal |author1=Philip E. Eaton |author2=Luigi Cassar |author3=Jack Halpern | title = Silver(I)- and palladium(II)-catalyzed isomerizations of cubane. Synthesis and characterization of cuneane | journal = Journal of the American Chemical Society | volume = 92 | issue = 21 | year = 1970 | pages = 6366–6368 | doi = 10.1021/ja00724a061 |bibcode=1970JAChS..92.6366E }} Similar reactions are known for () and bishomocubane ().{{cite journal |author1=Leo A. Paquette |author2=John C. Stowell | title = Silver ion catalyzed rearrangements of strained sigma. bonds. Application to the homocubyl and 1,1'-bishomocubyl systems | journal = Journal of the American Chemical Society | volume = 92 | issue = 8 | year = 1970 | pages = 2584–2586 | doi = 10.1021/ja00711a082 |bibcode=1970JAChS..92.2584P }}{{cite journal |author1=W. G. Dauben |author2=M. G. Buzzolini |author3=C. H. Schallhorn |author4=D. L. Whalen |author5=K. J. Palmer | title = Thermal and silver ion catalyzed isomerization of the 1,1′-bishomocubane system: preparation of a new C10H10 isomer | journal = Tetrahedron Letters | volume = 11 | issue = 10 | year = 1970 | pages = 787–790 | doi = 10.1016/S0040-4039(01)97830-X |author1=K. Kindler |author2=K. Lührs | title = Studien über den Mechanismus chemischer Reaktionen, XXIII. Hydrierungen von Nitrilen unter Verwendung von Terpenen als Wasserstoffdonatoren | journal = Chemische Berichte | volume = 99 | year = 1966 | pages = 227–232 | doi =10.1002/cber.19660990135

:[[File:CubaneToCun.png|thumb|left|300px|Synthesis of cuneane from cubane]]

Molecular geometry

The carbon atoms in the cuneane molecule form a hexahedron with point group C2v. The cuneane molecule has three kinds of equivalent carbon atoms (A, B, C), which have also been confirmed by NMR. The molecular graph of the carbon skeleton of cuneane is a regular graph with non-equivalent groups of vertices, and so it is a very important test object for different algorithms of mathematical chemistry.{{cite journal |author1=M.I. Trofimov |author2=E.A. Smolenskii | title = Electronegativity of atoms of ring-containing molecules—NMR spectroscopy data correlations: a description within the framework of the topological index approach | journal = Russian Chemical Bulletin | year = 2000 | volume = 49 | issue = 3 | pages = 402 | doi = 10.1007/BF02494766|s2cid=95809728 }}{{cite journal |author1=M.I. Trofimov |author2=E.A. Smolenskii | title = Application of the electronegativity indices of organic molecules to tasks of chemical informatics | journal = Russian Chemical Bulletin | year = 2005 | volume = 54 | issue = 9 | pages = 2235 | doi = 10.1007/s11172-006-0105-6|s2cid=98716956 }}

:[[File:Cuneane 2D.svg|thumb|left|120px|Equivalent carbon atoms in cuneane]]

Derivatives

Some cuneane derivatives have liquid crystal properties.{{cite journal |author1=Bényei, Gyula |author2=Jalsovszky, István |author3=Demus, Dietrich |author4=Prasad, Krishna |author5=Rao, Shankar |author6=Vajda, Anikó |author7=Jákli, Antal |author8=Fodor-Csorba, Katalin | title = First liquid crystalline cuneane-caged derivatives: a structure-property relationship study | journal = Liquid Crystals | year = 2006 | volume = 33 | issue = 6 | pages = 689–696 | doi = 10.1080/02678290600722940|bibcode=2006LoCr...33..689B |s2cid=97269476 }}

References

(1973). "Anwendungen der ¹³C-Resonanz-Spektroskopie, X. ¹³C,¹³C-Kopplungskonstanten in Methylencycloalkanen". [[Chemische Berichte]].

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