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Cubane

January 15, 2023

Cubane (C8H8) is a synthetic hydrocarbon compound that consists of eight carbon atoms arranged at the corners of a cube, with one hydrogen atom attached to each carbon atom. A solid crystalline substance, cubane is one of the Platonic hydrocarbons and a member of the prismanes. It was first synthesized in 1964 by Philip Eaton and Thomas Cole.[3] Before this work, Eaton believed that cubane would be impossible to synthesize due to the "required 90 degree bond angles".[4][5] The cubic shape requires the carbon atoms to adopt an unusually sharp 90° bonding angle, which would be highly strained as compared to the 109.45° angle of a tetrahedral carbon. Once formed, cubane is quite kinetically stable, due to a lack of readily available decomposition paths. It is the simplest hydrocarbon with octahedral symmetry.

Cubane
Names
Preferred IUPAC name
Cubane[1]
Systematic IUPAC name
Pentacyclo[4.2.0.02,5.03,8.04,7]octane
Identifiers
  • 277-10-1 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:33014 Y
ChemSpider
  • 119867 Y
  • 136090
UNII
  • Z5HM0Q7DK1 Y
  • DTXSID50182062
  • InChI=1S/C8H8/c1-2-5-3(1)7-4(1)6(2)8(5)7/h1-8H Y
    Key: TXWRERCHRDBNLG-UHFFFAOYSA-N Y
  • InChI=1/C8H8/c1-2-5-3(1)7-4(1)6(2)8(5)7/h1-8H
    Key: TXWRERCHRDBNLG-UHFFFAOYAL
  • C12C3C4C1C5C2C3C45
Properties
C8H8
Molar mass 104.15 g/mol
Density 1.29 g/cm3
Melting point 133.5 °C (272.3 °F; 406.6 K)[2]
Boiling point 161.6 °C (322.9 °F; 434.8 K)[2]
Related compounds
Related hydrocarbons
 Cuneane
Dodecahedrane
Tetrahedrane
Prismane
Prismane C8
Related compounds
 Octafluorocubane
Octanitrocubane
Octaazacubane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)

Having high potential energy but kinetic stability makes cubane and its derivative compounds useful for controlled energy storage. For example, octanitrocubane and heptanitrocubane have been studied as high-performance explosives.

These compounds also typically have a very high density for hydrocarbon molecules. The resulting high energy density means a large amount of energy can be stored in a comparably small amount of space, an important consideration for applications in fuel storage and energy transport.

Synthesis

The classic 1964 synthesis starts with the conversion of 2-cyclopentenone to 2-bromocyclopentadienone:[3][6]

 

Allylic bromination with N-bromosuccinimide in carbon tetrachloride followed by addition of molecular bromine to the alkene gives a 2,3,4-tribromocyclopentanone. Treating this compound with diethylamine in diethyl ether causes elimination of two equivalents of hydrogen bromide to give the diene product.

 
Eaton's 1964 synthesis of cubane

The construction of the eight-carbon cubane framework begins when 2-bromocyclopentadienone undergoes a spontaneous Diels-Alder dimerization. One ketal of the endo isomer is subsequently selectively deprotected with aqueous hydrochloric acid to 3.

In the next step, the endo isomer 3 (with both alkene groups in close proximity) forms the cage-like isomer 4 in a photochemical [2+2] cycloaddition. The bromoketone group is converted to ring-contracted carboxylic acid 5 in a Favorskii rearrangement with potassium hydroxide. Next, the thermal decarboxylation takes place through the acid chloride (with thionyl chloride) and the tert-butyl perester 6 (with tert-butyl hydroperoxide and 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 to give a tribromocyclopentanone derivative. Subsequent steps involve dehydrobromination, Diels-Alder dimerization, etc.[7][8]

 

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).[9]

Derivatives

See also: Cubane-type cluster

The synthesis of the octaphenyl derivative from tetraphenylcyclobutadiene nickel bromide by Freedman in 1962 pre-dates that of the parent compound. It is a sparingly soluble colourless compound that melts at 425–427 °C.[2][10][11][12] A hypercubane, with a hypercube-like structure, was predicted to exist in a 2014 publication.[13][14] Two different isomers of cubene have been synthesized, and a third analyzed computationally. The alkene in ortho-cubene is exceptionally reactive due to its pyramidalized geometry. At the time of its synthesis, this was the most pyramidalized alkene to have been successfully made.[15] The meta-cubene isomer is even less stable, and the para-cubene isomer probably only exists as a diradical rather than an actual diagonal bond.[16]

In 2022, both heptafluorocubane and octafluorocubane were synthesized.[17] Octafluorocubane is of theoretical interest because of its unusual electronic structure,[18] which is indicated by its susceptibility to undergo reduction to a detectable anion C
8F−
8, with a free electron trapped inside the cube.[19]

Cubylcubanes and oligocubanes

Cubene (1,2-dehydrocubane) and 1,4-cubanediyl(1,4-dehydrocubane) are enormously strained compounds which both undergo nucleophilic addition very rapidly, and this has enabled chemists to synthesize cubylcubane. X-ray diffraction structure solution has shown that the central cubylcubane 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 and close to the nucleus.[20] Chemists at the University of Chicago extended and modified the sequence in a way that permits the preparation of a host of [n]cubylcubane oligomers.[21] The [n]cubylcubanes are rigid molecular rods with the particular promise at the time of making liquid crystals with exceptional UV transparency. As the number of linked cubane units increases, the solubility of [n]cubylcubane plunges; as a result, only limited chain length (up to 40 units) have been successfully synthesized in solutions. The skeleton of [n]cubylcubanes is still composed of enormously strained carbon cubes, which therefore limit its stability. In contrast, researchers at Penn State University showed that poly-cubane synthesized by solid-state reaction is 100% sp3 carbon bonded with a tetrahedral angle (109.5°) and exhibits exceptional optical properties (high refractive index). [22]

Reactions

Cuneane may be produced from cubane by a metal-ion-catalyzed σ-bond rearrangement.[23][24]

 

With a rhodium catalyst, it first forms syn-tricyclooctadiene, which can thermally decompose to cyclooctatetraene at 50–60 °C.[25]

 

See also

References

  1. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 169. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. The retained names adamantane and cubane are used in general nomenclature and as preferred IUPAC names.
  2. ^ a b c Biegasiewicz, Kyle; Griffiths, Justin; Savage, G. Paul; Tsanakstidis, John; Priefer, Ronny (2015). "Cubane: 50 years later". Chemical Reviews. 115 (14): 6719–6745. doi:10.1021/cr500523x. PMID 26102302.
  3. ^ a b Eaton, Philip E.; Cole, Thomas W. (1964). "Cubane". J. Am. Chem. Soc. 86 (15): 3157–3158. doi:10.1021/ja01069a041.
  4. ^ Teachers, University of New South Wales Summer School for Chemistry (1963). Approach to Chemistry: Lectures and Workshop Reports of the ... Summer School for Chemistry Teachers. The University. p. 98. "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."
  5. ^ Moore, John W.; Stanitski, Conrad L.; Jurs, Peter C. (2002). Chemistry: The Molecular Science. Harcourt College Publishers. p. 372. ISBN 978-0-03-032011-8. "This sharp bond angle creates severe bond strain in cubane, a compound thought previously impossible to synthesize because of the required 90° bond angles."
  6. ^ Eaton, Philip E.; Cole, Thomas W. (1964). "The Cubane System". J. Am. Chem. Soc. 86 (5): 962–964. doi:10.1021/ja01059a072.
  7. ^ Bliese, Marianne; Tsanaktsidis, John (1997). "Dimethyl Cubane-1,4-dicarboxylate: A Practical Laboratory Scale Synthesis". Australian Journal of Chemistry. 50 (3): 189. doi:10.1071/C97021.
  8. ^ Fluorochem, Inc (July 1989). "Cubane Derivatives for Propellant Applications" (PDF). (PDF) from the original on 2021-07-09. {{cite web}}: |first= has generic name (help)
  9. ^ Eaton, Philip E. (1992). "Cubane: Ausgangsverbindungen für die Chemie der neunziger Jahre und des nächsten Jahrhunderts". Angewandte Chemie (in German). 104 (11): 1447–1462. Bibcode:1992AngCh.104.1447E. doi:10.1002/ange.19921041105.
  10. ^ Freedman, H. H. (1961). "Tetraphenylcyclobutadiene Derivatives. II.1 Chemical Evidence for the Triplet State". J. Am. Chem. Soc. 83 (9): 2195–2196. doi:10.1021/ja01470a037.
  11. ^ Freedman, H. H.; Petersen, D. R. (1962). "Tetraphenylcyclobutadiene Derivatives. IV.1 "Octaphenylcubane"; A Dimer of Tetraphenylcyclobutadiene". J. Am. Chem. Soc. 84 (14): 2837–2838. doi:10.1021/ja00873a046.
  12. ^ Pawley, G. S.; Lipscomb, W. N.; Freedman, H. H. (1964). "Structure of the Dimer of tetraphenylcyclobutadiene". J. Am. Chem. Soc. 86 (21): 4725–4726. doi:10.1021/ja01075a042.
  13. ^ Pichierri, F. (2014). "Hypercubane: DFT-based prediction of an Oh-symmetric double-shell hydrocarbon". Chem. Phys. Lett. 612: 198–202. Bibcode:2014CPL...612..198P. doi:10.1016/j.cplett.2014.08.032.
  14. ^ "Hypercubane: DFT-based prediction of an Oh-symmetric double-shell hydrocarbon".
  15. ^ Eaton, Philip E.; Maggini, Michele (1988). "Cubene (1,2-dehydrocubane)". J. Am. Chem. Soc. 110 (21): 7230–7232. doi:10.1021/ja00229a057.
  16. ^ Minyaev, Ruslan M.; Minkin, Vladimir I.; Gribanova, Tatyana N. (2009). "2.3 A Theoretical Approach to the Study and Design of Prismane Systems". In Dodziuk, Helena (ed.). Strained Hydrocarbons. Wiley. p. 55. ISBN 9783527627141.
  17. ^ Sugiyama M, Akiyama M, Yonezawa Y, Komaguchi K, Higashi M, Nozaki K, Okazoe T (August 2022). "Electron in a cube: Synthesis and characterization of perfluorocubane as an electron acceptor". Science. 377 (6607): 756–759. doi:10.1126/science.abq0516. PMID 35951682. S2CID 251515925.
  18. ^ Pichierri, 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
  19. ^ Krafft MP, Riess JG (August 2022). "Perfluorocubane-a tiny electron guzzler". Science. 377 (6607): 709. doi:10.1126/science.adc9195. PMID 35951708. S2CID 251517529.
  20. ^ Gilardi, Richard.; Maggini, Michele.; Eaton, Philip E. (1 October 1988). "X-ray structures of cubylcubane and 2-tert-butylcubylcubane: short cage-cage bonds". Journal of the American Chemical Society. 110 (21): 7232–7234. doi:10.1021/ja00229a058. ISSN 0002-7863.
  21. ^ Eaton, Philip E. (1992). "Cubanes: Starting Materials for the Chemistry of the 1990s and the New Century". Angewandte Chemie International Edition in English. 31 (11): 1421–1436. doi:10.1002/anie.199214211. ISSN 1521-3773.
  22. ^ Huang, Haw-Tyng; Zhu, Li; Ward, Matthew D.; Wang, Tao; Chen, Bo; Chaloux, Brian L.; Wang, Qianqian; Biswas, Arani; Gray, Jennifer L.; Kuei, Brooke; Cody, George D.; Epshteyn, Albert; Crespi, Vincent H.; Badding, John V.; Strobel, Timothy A. (21 January 2020). "Nanoarchitecture through Strained Molecules: Cubane-Derived Scaffolds and the Smallest Carbon Nanothreads". Journal of the American Chemical Society. 142 (42): 17944–17955. doi:10.1021/jacs.9b12352. ISSN 0002-7863. PMID 31961671. S2CID 210870993.
  23. ^ Smith, Michael B.; March, Jerry (2001). March's Advanced Organic Chemistry (5th ed.). John Wiley & Sons. p. 1459. ISBN 0-471-58589-0.
  24. ^ Kindler, K.; Lührs, K. (1966). "Studien über den Mechanismus chemischer Reaktionen, XXIII. Hydrierungen von Nitrilen unter Verwendung von Terpenen als Wasserstoffdonatoren". Chem. Ber. 99: 227–232. doi:10.1002/cber.19660990135.
  25. ^ Cassar, Luigi; Eaton, Philip E.; Halpern, Jack (1970). "Catalysis of symmetry-restricted reactions by transition metal compounds. Valence isomerization of cubane". Journal of the American Chemical Society. 92 (11): 3515–3518. doi:10.1021/ja00714a075. ISSN 0002-7863.

External links

  • Eaton's cubane synthesis at SynArchive.com
  • Tsanaktsidis's cubane synthesis at SynArchive.com
  • Cubane chemistry at Imperial College London

January 15, 2023
cubane, c8h8, synthetic, hydrocarbon, compound, that, consists, eight, carbon, atoms, arranged, corners, cube, with, hydrogen, atom, attached, each, carbon, atom, solid, crystalline, substance, cubane, platonic, hydrocarbons, member, prismanes, first, synthesi. Cubane C8H8 is a synthetic hydrocarbon compound that consists of eight carbon atoms arranged at the corners of a cube with one hydrogen atom attached to each carbon atom A solid crystalline substance cubane is one of the Platonic hydrocarbons and a member of the prismanes It was first synthesized in 1964 by Philip Eaton and Thomas Cole 3 Before this work Eaton believed that cubane would be impossible to synthesize due to the required 90 degree bond angles 4 5 The cubic shape requires the carbon atoms to adopt an unusually sharp 90 bonding angle which would be highly strained as compared to the 109 45 angle of a tetrahedral carbon Once formed cubane is quite kinetically stable due to a lack of readily available decomposition paths It is the simplest hydrocarbon with octahedral symmetry Cubane NamesPreferred IUPAC name Cubane 1 Systematic IUPAC name Pentacyclo 4 2 0 02 5 03 8 04 7 octaneIdentifiersCAS Number 277 10 1 Y3D model JSmol Interactive imageChEBI CHEBI 33014 YChemSpider 119867 YPubChem CID 136090UNII Z5HM0Q7DK1 YCompTox Dashboard EPA DTXSID50182062InChI InChI 1S C8H8 c1 2 5 3 1 7 4 1 6 2 8 5 7 h1 8H YKey TXWRERCHRDBNLG UHFFFAOYSA N YInChI 1 C8H8 c1 2 5 3 1 7 4 1 6 2 8 5 7 h1 8HKey TXWRERCHRDBNLG UHFFFAOYALSMILES C12C3C4C1C5C2C3C45PropertiesChemical formula C8H8Molar mass 104 15 g molDensity 1 29 g cm3Melting point 133 5 C 272 3 F 406 6 K 2 Boiling point 161 6 C 322 9 F 434 8 K 2 Related compoundsRelated hydrocarbons CuneaneDodecahedraneTetrahedranePrismanePrismane C8Related compounds OctafluorocubaneOctanitrocubaneOctaazacubaneExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Having high potential energy but kinetic stability makes cubane and its derivative compounds useful for controlled energy storage For example octanitrocubane and heptanitrocubane have been studied as high performance explosives These compounds also typically have a very high density for hydrocarbon molecules The resulting high energy density means a large amount of energy can be stored in a comparably small amount of space an important consideration for applications in fuel storage and energy transport Contents 1 Synthesis 2 Derivatives 3 Cubylcubanes and oligocubanes 4 Reactions 5 See also 6 References 7 External linksSynthesis EditThe classic 1964 synthesis starts with the conversion of 2 cyclopentenone to 2 bromocyclopentadienone 3 6 Allylic bromination with N bromosuccinimide in carbon tetrachloride followed by addition of molecular bromine to the alkene gives a 2 3 4 tribromocyclopentanone Treating this compound with diethylamine in diethyl ether causes elimination of two equivalents of hydrogen bromide to give the diene product Eaton s 1964 synthesis of cubaneThe construction of the eight carbon cubane framework begins when 2 bromocyclopentadienone undergoes a spontaneous Diels Alder dimerization One ketal of the endo isomer is subsequently selectively deprotected with aqueous hydrochloric acid to 3 In the next step the endo isomer 3 with both alkene groups in close proximity forms the cage like isomer 4 in a photochemical 2 2 cycloaddition The bromoketone group is converted to ring contracted carboxylic acid 5 in a Favorskii rearrangement with potassium hydroxide Next the thermal decarboxylation takes place through the acid chloride with thionyl chloride and the tert butyl perester 6 with tert butyl hydroperoxide and 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 to give a tribromocyclopentanone derivative Subsequent steps involve dehydrobromination Diels Alder dimerization etc 7 8 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 9 Derivatives EditSee also Cubane type cluster The synthesis of the octaphenyl derivative from tetraphenylcyclobutadiene nickel bromide by Freedman in 1962 pre dates that of the parent compound It is a sparingly soluble colourless compound that melts at 425 427 C 2 10 11 12 A hypercubane with a hypercube like structure was predicted to exist in a 2014 publication 13 14 Two different isomers of cubene have been synthesized and a third analyzed computationally The alkene in ortho cubene is exceptionally reactive due to its pyramidalized geometry At the time of its synthesis this was the most pyramidalized alkene to have been successfully made 15 The meta cubene isomer is even less stable and the para cubene isomer probably only exists as a diradical rather than an actual diagonal bond 16 In 2022 both heptafluorocubane and octafluorocubane were synthesized 17 Octafluorocubane is of theoretical interest because of its unusual electronic structure 18 which is indicated by its susceptibility to undergo reduction to a detectable anion C8 F 8 with a free electron trapped inside the cube 19 Cubylcubanes and oligocubanes EditCubene 1 2 dehydrocubane and 1 4 cubanediyl 1 4 dehydrocubane are enormously strained compounds which both undergo nucleophilic addition very rapidly and this has enabled chemists to synthesize cubylcubane X ray diffraction structure solution has shown that the central cubylcubane bond is exceedingly short 1 458 A much shorter than the typical C C single bond 1 578 A This is attributed to the fact that the exocyclic orbitals of cubane are s rich and close to the nucleus 20 Chemists at the University of Chicago extended and modified the sequence in a way that permits the preparation of a host of n cubylcubane oligomers 21 The n cubylcubanes are rigid molecular rods with the particular promise at the time of making liquid crystals with exceptional UV transparency As the number of linked cubane units increases the solubility of n cubylcubane plunges as a result only limited chain length up to 40 units have been successfully synthesized in solutions The skeleton of n cubylcubanes is still composed of enormously strained carbon cubes which therefore limit its stability In contrast researchers at Penn State University showed that poly cubane synthesized by solid state reaction is 100 sp3 carbon bonded with a tetrahedral angle 109 5 and exhibits exceptional optical properties high refractive index 22 Reactions EditCuneane may be produced from cubane by a metal ion catalyzed s bond rearrangement 23 24 With a rhodium catalyst it first forms syn tricyclooctadiene which can thermally decompose to cyclooctatetraene at 50 60 C 25 See also EditBasketaneReferences Edit Nomenclature of Organic Chemistry IUPAC Recommendations and Preferred Names 2013 Blue Book Cambridge The Royal Society of Chemistry 2014 p 169 doi 10 1039 9781849733069 FP001 ISBN 978 0 85404 182 4 The retained names adamantane and cubane are used in general nomenclature and as preferred IUPAC names a b c Biegasiewicz Kyle Griffiths Justin Savage G Paul Tsanakstidis John Priefer Ronny 2015 Cubane 50 years later Chemical Reviews 115 14 6719 6745 doi 10 1021 cr500523x PMID 26102302 a b Eaton Philip E Cole Thomas W 1964 Cubane J Am Chem Soc 86 15 3157 3158 doi 10 1021 ja01069a041 Teachers University of New South Wales Summer School for Chemistry 1963 Approach to Chemistry Lectures and Workshop Reports of the Summer School for Chemistry Teachers The University p 98 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 Moore John W Stanitski Conrad L Jurs Peter C 2002 Chemistry The Molecular Science Harcourt College Publishers p 372 ISBN 978 0 03 032011 8 This sharp bond angle creates severe bond strain in cubane a compound thought previously impossible to synthesize because of the required 90 bond angles Eaton Philip E Cole Thomas W 1964 The Cubane System J Am Chem Soc 86 5 962 964 doi 10 1021 ja01059a072 Bliese Marianne Tsanaktsidis John 1997 Dimethyl Cubane 1 4 dicarboxylate A Practical Laboratory Scale Synthesis Australian Journal of Chemistry 50 3 189 doi 10 1071 C97021 Fluorochem Inc July 1989 Cubane Derivatives for Propellant Applications PDF Archived PDF from the original on 2021 07 09 a href Template Cite web html title Template Cite web cite web a first has generic name help Eaton Philip E 1992 Cubane Ausgangsverbindungen fur die Chemie der neunziger Jahre und des nachsten Jahrhunderts Angewandte Chemie in German 104 11 1447 1462 Bibcode 1992AngCh 104 1447E doi 10 1002 ange 19921041105 Freedman H H 1961 Tetraphenylcyclobutadiene Derivatives II 1 Chemical Evidence for the Triplet State J Am Chem Soc 83 9 2195 2196 doi 10 1021 ja01470a037 Freedman H H Petersen D R 1962 Tetraphenylcyclobutadiene Derivatives IV 1 Octaphenylcubane A Dimer of Tetraphenylcyclobutadiene J Am Chem Soc 84 14 2837 2838 doi 10 1021 ja00873a046 Pawley G S Lipscomb W N Freedman H H 1964 Structure of the Dimer of tetraphenylcyclobutadiene J Am Chem Soc 86 21 4725 4726 doi 10 1021 ja01075a042 Pichierri F 2014 Hypercubane DFT based prediction of an Oh symmetric double shell hydrocarbon Chem Phys Lett 612 198 202 Bibcode 2014CPL 612 198P doi 10 1016 j cplett 2014 08 032 Hypercubane DFT based prediction of an Oh symmetric double shell hydrocarbon Eaton Philip E Maggini Michele 1988 Cubene 1 2 dehydrocubane J Am Chem Soc 110 21 7230 7232 doi 10 1021 ja00229a057 Minyaev Ruslan M Minkin Vladimir I Gribanova Tatyana N 2009 2 3 A Theoretical Approach to the Study and Design of Prismane Systems In Dodziuk Helena ed Strained Hydrocarbons Wiley p 55 ISBN 9783527627141 Sugiyama M Akiyama M Yonezawa Y Komaguchi K Higashi M Nozaki K Okazoe T August 2022 Electron in a cube Synthesis and characterization of perfluorocubane as an electron acceptor Science 377 6607 756 759 doi 10 1126 science abq0516 PMID 35951682 S2CID 251515925 Pichierri 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 Krafft MP Riess JG August 2022 Perfluorocubane a tiny electron guzzler Science 377 6607 709 doi 10 1126 science adc9195 PMID 35951708 S2CID 251517529 Gilardi Richard Maggini Michele Eaton Philip E 1 October 1988 X ray structures of cubylcubane and 2 tert butylcubylcubane short cage cage bonds Journal of the American Chemical Society 110 21 7232 7234 doi 10 1021 ja00229a058 ISSN 0002 7863 Eaton Philip E 1992 Cubanes Starting Materials for the Chemistry of the 1990s and the New Century Angewandte Chemie International Edition in English 31 11 1421 1436 doi 10 1002 anie 199214211 ISSN 1521 3773 Huang Haw Tyng Zhu Li Ward Matthew D Wang Tao Chen Bo Chaloux Brian L Wang Qianqian Biswas Arani Gray Jennifer L Kuei Brooke Cody George D Epshteyn Albert Crespi Vincent H Badding John V Strobel Timothy A 21 January 2020 Nanoarchitecture through Strained Molecules Cubane Derived Scaffolds and the Smallest Carbon Nanothreads Journal of the American Chemical Society 142 42 17944 17955 doi 10 1021 jacs 9b12352 ISSN 0002 7863 PMID 31961671 S2CID 210870993 Smith Michael B March Jerry 2001 March s Advanced Organic Chemistry 5th ed John Wiley amp Sons p 1459 ISBN 0 471 58589 0 Kindler K Luhrs K 1966 Studien uber den Mechanismus chemischer Reaktionen XXIII Hydrierungen von Nitrilen unter Verwendung von Terpenen als Wasserstoffdonatoren Chem Ber 99 227 232 doi 10 1002 cber 19660990135 Cassar Luigi Eaton Philip E Halpern Jack 1970 Catalysis of symmetry restricted reactions by transition metal compounds Valence isomerization of cubane Journal of the American Chemical Society 92 11 3515 3518 doi 10 1021 ja00714a075 ISSN 0002 7863 External links EditEaton s cubane synthesis at SynArchive com Tsanaktsidis s cubane synthesis at SynArchive com Cubane chemistry at Imperial College London Retrieved from https en wikipedia org w index php title Cubane amp oldid 1131125987, wikipedia, wiki, book, books, library,

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