# Cubane > Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Cubane > Markdown URL: https://mediated.wiki/source/Cubane.md > Source: https://en.wikipedia.org/wiki/Cubane > Source revision: 1355706567 > License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/) {{Short description|Organic compound (C8H8) with a cube carbon structure}} {{chembox | Watchedfields = changed | verifiedrevid = 443545029 | Name = Cubane | ImageFile = Cuban.svg | ImageClass = skin-invert-image | ImageFileL1 = cubane-cpk.png | ImageClassL1 = bg-transparent | ImageNameL1 = CPK model of Cubane. | ImageFileR1 = Cubane molecule ball.png | ImageClassR1 = bg-transparent | ImageName = Structural formula of cubane | ImageNameR1 = Ball-and-stick model of cubane | PIN = Cubane{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [The Royal Society of Chemistry](/source/Royal_Society_of_Chemistry) | date = 2014 | location = Cambridge | page = 169 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4 | quote = The retained names adamantane and cubane are used in general nomenclature and as preferred IUPAC names.}} | SystematicName = Pentacyclo[4.2.0.02,5.03,8.04,7]octane | OtherNames = | Section1 = {{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 119867 | PubChem = 136090 | InChIKey = TXWRERCHRDBNLG-UHFFFAOYAL | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C8H8/c1-2-5-3(1)7-4(1)6(2)8(5)7/h1-8H | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = TXWRERCHRDBNLG-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|??}} | CASNo = 277-10-1 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = Z5HM0Q7DK1 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 33014 | SMILES = C12C3C4C1C5C2C3C45 | InChI = 1/C8H8/c1-2-5-3(1)7-4(1)6(2)8(5)7/h1-8H }} | Section2 = {{Chembox Properties | Formula = {{chem2|C8H8}} | MolarMass = 104.15 g/mol | Density = 1.29 g/cm3 | Appearance = Transparent{{cite web | url=https://www.ch.ic.ac.uk/local/projects/b_muir/Cubane/Cubanepro/Start.html | title=Start }} crystalline solid | MeltingPtC = 133.5 | MeltingPt_ref = | BoilingPtC = 161.6 | BoilingPt_ref = }} | Section8 = {{Chembox Related | OtherFunction = [Cuneane](/source/Cuneane)
[Dodecahedrane](/source/Dodecahedrane)
[Tetrahedrane](/source/Tetrahedrane)
[Prismane](/source/Prismane)
[Prismane C8](/source/Prismane_C8) | OtherFunction_label = [hydrocarbon](/source/hydrocarbon)s | OtherCompounds = [Octafluorocubane](/source/Octafluorocubane)
[Octanitrocubane](/source/Octanitrocubane)
[Octaazacubane](/source/Octaazacubane)
[Mirex](/source/Mirex) }} }} '''Cubane''' is a synthetic [hydrocarbon](/source/hydrocarbon) compound with the [formula](/source/Chemical_formula) {{chem2|C8H8}}. It consists of eight [carbon](/source/carbon) atoms arranged at the corners of a [cube](/source/Cube_(geometry)), with one [hydrogen](/source/hydrogen) atom attached to each carbon atom. A solid [crystal](/source/crystal)line substance, cubane is one of the [Platonic hydrocarbon](/source/Platonic_hydrocarbon)s and a member of the [prismanes](/source/prismanes). It was first synthesized in 1964 by [Philip Eaton](/source/Philip_Eaton) and Thomas Cole. Before this work, Eaton believed that cubane would be impossible to synthesize due to the "required 90 degree [bond angles](/source/molecular_geometry)".{{cite book |last1=Teachers |first1=University of New South Wales Summer School for Chemistry |title=Approach to Chemistry: Lectures and Workshop Reports of the ... Summer School for Chemistry Teachers |date=1963 |publisher=The University |page=98 |url=https://books.google.com/books?id=cFA0AQAAIAAJ |language=en}} "This compound was described only a few months ago and, curiously enough, it is quite easy to make, although only a year ago I would have predicted that it would be difficult, or even impossible, to synthesize."{{cite book |last1=Moore |first1=John W. |last2=Stanitski |first2=Conrad L. |last3=Jurs |first3=Peter C. |title=Chemistry: The Molecular Science |date=2002 |publisher=Harcourt College Publishers |isbn=978-0-03-032011-8 |page=372 |url=https://books.google.com/books?id=XjcvAQAAIAAJ |language=en}} "This sharp bond angle creates severe bond strain in cubane, a compound thought previously impossible to synthesize because of the required 90° bond angles." The cubic shape requires the carbon atoms to adopt an unusually sharp 90° bonding angle, which would be highly [strained](/source/strain_(chemistry)) as compared to the [109.45° angle](/source/tetrahedral_molecular_geometry) of a [tetrahedral](/source/tetrahedral_geometry) carbon. Once formed, cubane is quite [kinetically stable](/source/kinetic_stability), due to a lack of readily available decomposition paths. It is the simplest hydrocarbon with [octahedral symmetry](/source/octahedral_symmetry). Having high potential energy and kinetic stability makes cubane and its derivative compounds useful for controlled energy storage. For example, [octanitrocubane](/source/octanitrocubane) and [heptanitrocubane](/source/heptanitrocubane) have been studied as high-performance explosives. These compounds also typically have a very high [density](/source/density) for hydrocarbon molecules. The resulting high [energy density](/source/energy_density) means a large amount of energy can be stored in a comparably smaller amount of space, an important consideration for applications in fuel storage and energy transport. Furthermore, their geometry and stability make them suitable [isostere](/source/isostere)s for benzene rings.{{Cite journal |last1=Wiesenfeldt |first1=Mario P. |last2=Rossi-Ashton |first2=James A. |last3=Perry |first3=Ian B. |last4=Diesel |first4=Johannes |last5=Garry |first5=Olivia L. |last6=Bartels |first6=Florian |last7=Coote |first7=Susannah C. |last8=Ma |first8=Xiaoshen |last9=Yeung |first9=Charles S. |last10=Bennett |first10=David J. |last11=MacMillan |first11=David W. C. |date=June 2023 |title=General access to cubanes as benzene bioisosteres |journal=Nature |language=en |volume=618 |issue=7965 |pages=513–518 |doi=10.1038/s41586-023-06021-8 |pmid=37015289 |issn=1476-4687|pmc=10680098 |bibcode=2023Natur.618..513W }} ==Synthesis== The classic 1964 synthesis starts with the conversion of [2-cyclopentenone](/source/2-cyclopentenone) to 2-bromo[cyclopentadienone](/source/cyclopentadienone): 500px|class=skin-invert [Allylic](/source/Allylic) [bromination](/source/bromination) with [''N''-bromosuccinimide](/source/N-Bromosuccinimide) in [carbon tetrachloride](/source/carbon_tetrachloride) followed by addition of molecular bromine to the [alkene](/source/alkene) gives a 2,3,4-tribromocyclopentanone. Treating this compound with [diethylamine](/source/diethylamine) in [diethyl ether](/source/diethyl_ether) causes [elimination](/source/elimination_reaction) of two equivalents of [hydrogen bromide](/source/hydrogen_bromide) to give the diene product. thumb| class=skin-invert-image|left|500px|Eaton's 1964 synthesis of cubane{{clear left}} The construction of the eight-carbon cubane framework begins when 2-bromocyclopentadienone undergoes a spontaneous [Diels-Alder dimerization](/source/Diels-Alder_reaction). One ketal of the [''endo'' isomer](/source/Endo-exo_isomerism) is subsequently selectively deprotected with aqueous [hydrochloric acid](/source/hydrochloric_acid) to '''3'''. In the next step, the ''endo'' isomer '''3''' (with both [alkene](/source/alkene) groups in close proximity) forms the cage-like isomer '''4''' in a [photochemical](/source/photochemical) [2+2] [cycloaddition](/source/cycloaddition). The [bromoketone](/source/haloketone) group is converted to ring-contracted [carboxylic acid](/source/carboxylic_acid) '''5''' in a [Favorskii rearrangement](/source/Favorskii_rearrangement) with [potassium hydroxide](/source/potassium_hydroxide). Next, the thermal [decarboxylation](/source/decarboxylation) takes place through the [acid chloride](/source/acid_chloride) (with [thionyl chloride](/source/thionyl_chloride)) and the [''tert''-butyl](/source/tert-butyl) [perester](/source/perester) '''6''' (with [''tert''-butyl hydroperoxide](/source/Tert-Butyl_hydroperoxide) and [pyridine](/source/pyridine)) to '''7'''; afterward, the acetal is once more removed in '''8'''. A second Favorskii rearrangement gives '''9''', and finally another decarboxylation gives, via '''10''', cubane ('''11'''). A more approachable laboratory synthesis of disubstituted cubane involves bromination of the ethylene ketal of [cyclopentanone](/source/cyclopentanone) to give a tribromocyclopentanone derivative. Subsequent steps involve dehydrobromination, Diels-Alder dimerization, etc.{{Cite journal|doi=10.1071/C97021|title=Dimethyl Cubane-1,4-dicarboxylate: A Practical Laboratory Scale Synthesis|year=1997|last1=Bliese|first1=Marianne|last2=Tsanaktsidis|first2=John|journal=Australian Journal of Chemistry|volume=50|issue=3|page=189}}{{Cite web|author =Fluorochem, Inc|date=July 1989|title=Cubane Derivatives for Propellant Applications|url=https://apps.dtic.mil/sti/pdfs/ADA210368.pdf|url-status=live|archive-url=https://web.archive.org/web/20210709185435/https://apps.dtic.mil/sti/pdfs/ADA210368.pdf |archive-date=2021-07-09 }} Alternative synthesis of a disubstituted cubane|555x555px|class=skin-invert|center The resulting '''cubane-1,4-dicarboxylic acid''' is used to synthesize other substituted cubanes. Cubane itself can be obtained nearly quantitatively by photochemical decarboxylation of the thiohydroxamate ester (the [Barton decarboxylation](/source/Barton_decarboxylation)).{{Cite journal |last=Eaton |first=Philip E. |date=1992 |title=Cubane: Ausgangsverbindungen für die Chemie der neunziger Jahre und des nächsten Jahrhunderts |url=https://onlinelibrary.wiley.com/doi/10.1002/ange.19921041105 |journal=Angewandte Chemie |language=de |volume=104 |issue=11 |pages=1447–1462 |doi=10.1002/ange.19921041105|bibcode=1992AngCh.104.1447E |url-access=subscription }} ==Reactions and derivatives== [[File:Cubane locants.svg|class=skin-invert-image|right|thumb|80px|{{nowrap|Cubane [locant](/source/locant)s}}]] Cubane is highly strained, but cannot decompose because the resultant [cubene](/source/cubene) molecules are [pyramidal alkene](/source/pyramidal_alkene)s, too high-energy for most [elimination pathways](/source/elimination_reaction). Certain metallic ions [catalyze σ-bond rearrangement](/source/metal-ion-catalyzed_%CF%83-bond_rearrangement) to [cuneane](/source/cuneane): :176x176px|class=skin-invert With a [rhodium](/source/rhodium) catalyst, cubane first forms ''syn''-tricyclooctadiene, which can thermally decompose to [cyclooctatetraene](/source/cyclooctatetraene) at 50–60 °C.{{Cite journal |last1=Cassar |first1=Luigi |last2=Eaton |first2=Philip E. |last3=Halpern |first3=Jack |date=1970 |title=Catalysis of symmetry-restricted reactions by transition metal compounds. Valence isomerization of cubane |url=https://pubs.acs.org/doi/abs/10.1021/ja00714a075 |journal=Journal of the American Chemical Society |language=en |volume=92 |issue=11 |pages=3515–3518 |doi=10.1021/ja00714a075 |bibcode=1970JAChS..92.3515C |issn=0002-7863|url-access=subscription }} :400x400px|class=skin-invert The main cubane functionalization challenge is [C-H bond activation](/source/C-H_bond_activation). Cubenes still inhibit decomposition during [radical substitution](/source/radical_substitution), but the reaction offers little control against oversubstitution. In polar reactions, cubane reacts somewhat similarly to [arene](/source/arene)s or [other cluster compounds](/source/PSEPT): it [metallates](/source/metalation) easily.{{cite web|website=Cubane|first=B.|last=Muir|publisher=[Imperial College London](/source/Imperial_College_London)|title=Reactivity|url=https://www.ch.ic.ac.uk/local/projects/b_muir/Cubane/Cubanepro/Reactivity.html|access-date=22 May 2025|url-status=live|archive-url=https://web.archive.org/web/20240119125713/https://www.ch.ic.ac.uk/local/projects/b_muir/Cubane/Cubanepro/Reactivity.html|archive-date=19 Jan 2024}} Cubane is slightly [acidic](/source/carbon_acid), deprotonating about 63000 times faster than [cyclohexane](/source/cyclohexane).{{cite web|website=Cubane|first=B.|last=Muir|publisher=[Imperial College London](/source/Imperial_College_London)|title=Properties|at=The nature of the C–H bond|url=https://www.ch.ic.ac.uk/local/projects/b_muir/Cubane/Cubanepro/Properties.html|access-date=22 May 2025|url-status=live|archive-url=https://web.archive.org/web/20240119125716/https://www.ch.ic.ac.uk/local/projects/b_muir/Cubane/Cubanepro/Properties.html|archive-date=19 Jan 2024}} Cubane substituents generally display normal reactivity. For example a [Curtius rearrangement](/source/Curtius_rearrangement) followed by [organic oxidation](/source/organic_oxidation) converts {{chem name|cubane tetra(carbonylchloride)}} to [tetranitrocubane](/source/tetranitrocubane). However, [electron-rich](/source/electron-rich) substituents such as [alcohols](/source/alcohol_(chemistry)) can enable decomposition; they stabilize the cubene intermediate as a [ketone (or equivalent) tautomer](/source/keto-enol_tautomerism). [Oxalyl chloride](/source/Oxalyl_chloride) oxidizes cubane carboxamides to give a [norcubane](/source/norcubane)-[furanone](/source/furanone) derivative.{{cite journal|doi=10.1016/S0040-4039(97)10185-X|publisher=Pergamon (Elsevier)|journal=Tetrahedron Letters|volume=38|issue=47|pages=8137–8140|year=1997|title=Norcubanes from Cubanes: Novel reactions of amidocubanes with oxalyl chloride|first1=A.|last1=Bashir-Hashemi|first2=Nathan|last2=Gelber|first3=Richard|last3=Gilardi}} [Hypercubane](/source/Hypercubane) was predicted to exist in a 2014 publication.{{cite journal|last=Pichierri|first=F.|journal=Chem. Phys. Lett.|date=2014|volume=612|pages=198–202|doi=10.1016/j.cplett.2014.08.032|title= Hypercubane: DFT-based prediction of an ''Oh''-symmetric double-shell hydrocarbon|bibcode=2014CPL...612..198P}}{{Cite web | url=http://www.compchemhighlights.org/2014/12/hypercubane-dft-based-prediction-of-oh.html |title = Hypercubane: DFT-based prediction of an Oh-symmetric double-shell hydrocarbon}} ===Persubstituted derivatives=== Octaphenylcubane pre-dates the parent compound. Freedman synthesized it from [tetraphenylcyclobutadiene nickel bromide](/source/tetraphenylcyclobutadiene_nickel_bromide) in 1962. It is a sparingly soluble colourless compound that melts at 425–427 °C. [Octanitrocubane](/source/Octanitrocubane) is a [green explosive](/source/green_explosive). Both [heptafluorocubane](/source/heptafluorocubane) and [octafluorocubane](/source/octafluorocubane) were synthesized in 2022 to study octafluorocubane's unusual [electronic structure](/source/electronic_structure).{{cite journal |vauthors=Sugiyama M, Akiyama M, Yonezawa Y, Komaguchi K, Higashi M, Nozaki K, Okazoe T |date=August 2022 |title=Electron in a cube: Synthesis and characterization of perfluorocubane as an electron acceptor |journal=Science |volume=377 |issue=6607 |pages=756–759 |doi=10.1126/science.abq0516 |pmid=35951682 |bibcode=2022Sci...377..756S |s2cid=251515925}} Single-electron reduction to the [radical anion](/source/radical_anion) {{chem|C|8|F|8|-}} trapsPichierri, F. Substituent effects in cubane and hypercubane: a DFT and QTAIM study. ''Theor Chem Acc'' 2017; 136: 114. {{doi|10.1007/s00214-017-2144-5}} an otherwise-free electron inside the cube, making it the world's smallest box.{{cite journal |vauthors=Krafft MP, Riess JG |date=August 2022 |title=Perfluorocubane-a tiny electron guzzler |journal=Science |volume=377 |issue=6607 |pages=709 |doi=10.1126/science.adc9195 |pmid=35951708 |bibcode=2022Sci...377..709K |s2cid=251517529|url=https://hal.science/hal-03873082 }} ===Cubenes and oligo-cubylcubanes=== Despite their orbital strain, two cubenes have been synthesized, and a third analyzed [computationally](/source/computational_chemistry). {{ill|o-Cubene|lt=''ortho''-{{chem name|Cubene}}|qid=Q134578818|s=1}}, produced via [lithium-halogen exchange](/source/lithium-halogen_exchange) followed by elimination,{{cite web|website=Cubane|first=B.|last=Muir|publisher=[Imperial College London](/source/Imperial_College_London)|title=Further topics|url=https://www.ch.ic.ac.uk/local/projects/b_muir/Cubane/Cubanepro/FurtherTopics.html|access-date=22 May 2025|url-status=live|archive-url=https://web.archive.org/web/20240119125713/https://www.ch.ic.ac.uk/local/projects/b_muir/Cubane/Cubanepro/FurtherTopics.html|archive-date=19 January 2024}} was the most [pyramidalized](/source/pyramidal_alkene) alkene ever made at the time of its first synthesis.{{cite journal |title= Cubene (1,2-dehydrocubane) |first1= Philip E. |last1= Eaton |first2= Michele |last2= Maggini |journal= J. Am. Chem. Soc. |year= 1988 |volume= 110 |issue= 21 |pages= 7230–7232 |doi= 10.1021/ja00229a057 |bibcode= 1988JAChS.110.7230E }} In 2026, a new study of cubene was reported by [Garg](/source/Neil_Garg) and [Houk](/source/Kendall_Houk), showing that cubene has unusually low [bond order](/source/bond_order) and undergoes cycloadditions.{{Cite journal |last=Ding |first=Jiaming |last2=French |first2=Sarah A. |last3=Rivera |first3=Christina A. |last4=Tena Meza |first4=Arismel |last5=Witkowski |first5=Dominick C. |last6=Houk |first6=K. N. |last7=Garg |first7=Neil K. |date=2026-01-21 |title=Hyperpyramidalized alkenes with bond orders near 1.5 as synthetic building blocks |url=https://www.nature.com/articles/s41557-025-02055-9 |journal=Nature Chemistry |language=en |pages=1–10 |doi=10.1038/s41557-025-02055-9 |issn=1755-4349|doi-access=free }} ''Meta''-{{chem name|cubene}} (1,3-dehydrocubane) is even less stable, and ''para''-{{chem name|cubene}} (1,4-dehydrocubane) probably only exists as a [diradical](/source/diradical) rather than an actual diagonal bond.{{cite book |title= Strained Hydrocarbons |url= https://archive.org/details/strainedhydrocar00hypo_746 |url-access= limited |editor-first= Helena |editor-last= Dodziuk |chapter= 2.3 A Theoretical Approach to the Study and Design of Prismane Systems |first1= Ruslan M. |last1= Minyaev |first2= Vladimir I. |last2= Minkin |first3= Tatyana N. |last3= Gribanova |publisher= Wiley |year= 2009 |isbn= 9783527627141 |page=55}} They rapidly undergo [nucleophilic addition](/source/nucleophilic_addition). Decomposition of cubenes has enabled chemists to synthesize cubylcubane, as well as higher oligomers.{{cite journal |last1=Eaton |first1=Philip E. |title=Cubanes: Starting Materials for the Chemistry of the 1990s and the New Century |journal=Angewandte Chemie International Edition in English |date=1992 |volume=31 |issue=11 |pages=1421–1436 |doi=10.1002/anie.199214211 |language=en |issn=1521-3773}} Per [X-ray diffraction](/source/X-ray_diffraction), the central cubane-cubane bond is exceedingly short (1.458 Å), much shorter than the typical C-C single bond (1.578 Å). This is attributed to the fact that the exocyclic orbitals of cubane are [''s''-rich](/source/s_orbital) and close to the nucleus.{{cite journal |last1=Gilardi |first1=Richard. |last2=Maggini |first2=Michele. |last3=Eaton |first3=Philip E. |title=X-ray structures of cubylcubane and 2-tert-butylcubylcubane: short cage-cage bonds |journal=Journal of the American Chemical Society |date=1 October 1988 |volume=110 |issue=21 |pages=7232–7234 |doi=10.1021/ja00229a058 |bibcode=1988JAChS.110.7232G |issn=0002-7863}} The ''oligo''-cubylcubanes are rigid molecular rods considered for [liquid crystal](/source/liquid_crystal) design. Absent solubilizing groups on the cubane [monomer](/source/monomer), oligomers with at least 4 units are essentially insoluble, thus scarcely accessible through conventional [organic synthesis](/source/organic_synthesis).{{cite web|website=Cubane|first=B.|last=Muir|publisher=[Imperial College London](/source/Imperial_College_London)|title=Applications|at=Polymers|url=https://www.ch.ic.ac.uk/local/projects/b_muir/Cubane/Cubanepro/Applications.html|access-date=22 May 2025|url-status=live|archive-url=https://web.archive.org/web/20240508043615/https://www.ch.ic.ac.uk/local/projects/b_muir/Cubane/Cubanepro/Applications.html|archive-date=8 May 2024}} ===poly-cubane=== thumb|right|120px|class=skin-invert-image|Diasterane ''poly''-cubane may be synthesized via solid-state polymerization of cubane at 250 °C and high pressure (4–30 GPa) in a [diamond anvil cell](/source/diamond_anvil_cell), and is recoverable at ambient temperature and pressure.{{cite journal |last1=Huang |first1=Haw-Tyng |last2=Zhu |first2=Li |last3=Ward |first3=Matthew D. |last4=Wang |first4=Tao |last5=Chen |first5=Bo |last6=Chaloux |first6=Brian L. |last7=Wang |first7=Qianqian |last8=Biswas |first8=Arani |last9=Gray |first9=Jennifer L. |last10=Kuei |first10=Brooke |last11=Cody |first11=George D. |last12=Epshteyn |first12=Albert |last13=Crespi |first13=Vincent H. |last14=Badding |first14=John V. |last15=Strobel |first15=Timothy A. |title=Nanoarchitecture through Strained Molecules: Cubane-Derived Scaffolds and the Smallest Carbon Nanothreads |journal=Journal of the American Chemical Society |date=21 January 2020 |volume=142 |issue=42 |pages=17944–17955 |doi=10.1021/jacs.9b12352 |pmid=31961671 |bibcode=2020JAChS.14217944H |s2cid=210870993 |issn=0002-7863|url=https://par.nsf.gov/servlets/purl/10210835}} It is a translucent yellow crystalline solid, denser than cubane itself, that is stable up to 300 °C. Provisional structure assignment from [powder X-ray diffraction](/source/powder_X-ray_diffraction) suggests a model for the material that is formally derived from a 1D chain of cubane molecules by breaking two diametrically opposite C–C bonds in each cubane molecule to form a [diasterane](/source/asterane)-based tetraradical, then connecting each such group to the groups directly to its left and right via pairs of C–C bonds.{{rp|at=Figure 2}} It exhibits an exceptionally high [refractive index](/source/refractive_index).{{Failed verification|date=March 2026}} ==See also== *[Basketane](/source/Basketane) *[Tetrahedrane](/source/Tetrahedrane) *[Platonic hydrocarbon](/source/Platonic_hydrocarbon) *[Cubane-type cluster](/source/Cubane-type_cluster) ==References== {{reflist|colwidth=30em |refs= {{cite journal| last1 = Biegasiewicz | first1 = Kyle | last2 = Griffiths | first2 = Justin | last3 = Savage | first3 = G. Paul | last4 = Tsanakstidis | first4 = John | last5 = Priefer | first5 = Ronny | year = 2015 | title = Cubane: 50 years later | journal = Chemical Reviews| volume = 115 | issue = 14 | pages = 6719–6745 | doi=10.1021/cr500523x | pmid=26102302}} {{cite journal|title=Cubane|first1=Philip E.|last1=Eaton|first2=Thomas W.|last2=Cole|journal=[J. Am. Chem. Soc.](/source/J._Am._Chem._Soc.)|date=1964|volume=86|issue=15|pages=3157–3158|doi=10.1021/ja01069a041|bibcode=1964JAChS..86.3157E }} {{cite journal|title=The Cubane System|first1=Philip E.|last1=Eaton|first2=Thomas W.|last2=Cole|journal=[J. Am. Chem. Soc.](/source/J._Am._Chem._Soc.)|date=1964|volume=86|issue=5|pages=962–964|doi=10.1021/ja01059a072|bibcode=1964JAChS..86..962E }} {{cite book|first1=Michael B.|last1=Smith|first2=Jerry|last2=March|title=March's Advanced Organic Chemistry|url=https://archive.org/details/organicchemistry00mich_115|url-access=limited|edition=5th|publisher=John Wiley & Sons|date=2001|page=[https://archive.org/details/organicchemistry00mich_115/page/n1477 1459]|isbn=0-471-58589-0}} {{cite journal|title=Studien über den Mechanismus chemischer Reaktionen, XXIII. Hydrierungen von Nitrilen unter Verwendung von Terpenen als Wasserstoffdonatoren|first1=K.|last1=Kindler|first2=K.|last2=Lührs|journal=[Chem. Ber.](/source/Chem._Ber.)|volume=99|date=1966|pages=227–232|doi=10.1002/cber.19660990135}} {{cite journal|title=Tetraphenylcyclobutadiene Derivatives. II.1 Chemical Evidence for the Triplet State|first=H. H.|last=Freedman|journal=[J. Am. Chem. Soc.](/source/J._Am._Chem._Soc.)|date=1961|volume=83|issue=9|pages=2195–2196|doi=10.1021/ja01470a037|bibcode=1961JAChS..83.2195F }} {{cite journal|title=Tetraphenylcyclobutadiene Derivatives. IV.1 "Octaphenylcubane"; A Dimer of Tetraphenylcyclobutadiene|first1=H. H.|last1=Freedman|first2=D. R.|last2=Petersen|journal=[J. Am. Chem. Soc.](/source/J._Am._Chem._Soc.)|date=1962|volume=84|issue=14|pages=2837–2838|doi=10.1021/ja00873a046|bibcode=1962JAChS..84.2837F }} {{cite journal|title=Structure of the Dimer of tetraphenylcyclobutadiene|first1=G. S.|last1=Pawley|first2=W. N.|last2=Lipscomb|first3=H. H.|last3=Freedman|journal=[J. Am. Chem. Soc.](/source/J._Am._Chem._Soc.)|date=1964|volume=86|issue=21|pages=4725–4726|doi=10.1021/ja01075a042|bibcode=1964JAChS..86.4725P }} }} ==External links== * [http://www.synarchive.com/syn/14 Eaton's cubane synthesis at SynArchive.com] * [http://www.synarchive.com/syn/189 Tsanaktsidis's cubane synthesis at SynArchive.com] * [http://www.ch.ic.ac.uk/local/projects/b_muir/Cubane/Cubanepro/Start.html Cubane chemistry at Imperial College London] Category:Cubanes Category:Molecular geometry Category:Theoretical chemistry Category:Substances discovered in the 1960s Category:Pentacyclic compounds Category:Cubes Category:Polycyclic nonaromatic hydrocarbons --- Adapted from the Wikipedia article [Cubane](https://en.wikipedia.org/wiki/Cubane) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Cubane?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.