Dodecahedrane is a

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

, a

hydrocarbon In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and Hydrophobe, hydrophobic; their odor is usually fain ...

with formula , whose

carbon Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ...

atoms are arranged as the vertices (corners) of a regular

dodecahedron In geometry, a dodecahedron (; ) or duodecahedron is any polyhedron with twelve flat faces. The most familiar dodecahedron is the regular dodecahedron with regular pentagons as faces, which is a Platonic solid. There are also three Kepler–Po ...

. Each carbon is bound to three neighbouring carbon atoms and to a

hydrogen Hydrogen is a chemical element; it has chemical symbol, symbol H and atomic number 1. It is the lightest and abundance of the chemical elements, most abundant chemical element in the universe, constituting about 75% of all baryon, normal matter ...

atom. This compound is one of the three possible Platonic hydrocarbons, the other two being

cubane Cubane is a synthetic hydrocarbon compound with the Chemical formula, formula . It consists of eight carbon atoms arranged at the corners of a Cube (geometry), cube, with one hydrogen atom attached to each carbon atom. A solid crystalline substanc ...

and

tetrahedrane Tetrahedrane is a hypothetical platonic hydrocarbon with chemical formula and a tetrahedral structure. The molecule would be subject to considerable angle strain and has not been synthesized . However, a number of derivatives have been prepa ...

. Dodecahedrane does not occur in nature and has no significant uses. It was synthesized by Leo Paquette in 1982, primarily for the "aesthetically pleasing

symmetry Symmetry () in everyday life refers to a sense of harmonious and beautiful proportion and balance. In mathematics, the term has a more precise definition and is usually used to refer to an object that is Invariant (mathematics), invariant und ...

of the dodecahedral framework". For many years, dodecahedrane was the simplest real carbon-based

molecule A molecule is a group of two or more atoms that are held together by Force, attractive forces known as chemical bonds; depending on context, the term may or may not include ions that satisfy this criterion. In quantum physics, organic chemi ...

with full

icosahedral symmetry In mathematics, and especially in geometry, an object has icosahedral symmetry if it has the same symmetries as a regular icosahedron. Examples of other polyhedra with icosahedral symmetry include the regular dodecahedron (the dual polyhedr ...

Buckminsterfullerene Buckminsterfullerene is a type of fullerene with the formula . It has a cage-like fused-ring structure ( truncated icosahedron) made of twenty hexagons and twelve pentagons, and resembles a football. Each of its 60 carbon atoms is bonded to i ...

(), discovered in 1985, also has the same symmetry, but has three times as many carbons and 50% more atoms overall. The synthesis of the C₂₀ fullerene in 2000, from brominated dodecahedrane, may have demoted to second place.

Structure

The angle between the C-C bonds in each carbon atom is 108°, which is the angle between adjacent sides of a

regular pentagon In geometry, a pentagon () is any five-sided polygon or 5-gon. The sum of the internal angles in a simple polygon, simple pentagon is 540°. A pentagon may be simple or list of self-intersecting polygons, self-intersecting. A self-intersecting ...

. That value is quite close to the 109.5° central angle of a

regular tetrahedron In geometry, a tetrahedron (: tetrahedra or tetrahedrons), also known as a triangular pyramid, is a polyhedron composed of four triangular Face (geometry), faces, six straight Edge (geometry), edges, and four vertex (geometry), vertices. The tet ...

—the ideal angle between the bonds on an atom that has sp³ hybridisation. As a result, there is minimal angle strain. However, the molecule has significant levels of torsional strain as a result of the eclipsed conformation along each edge of the structure. The molecule has perfect icosahedral (I_h)

, as evidenced by its

proton NMR Proton nuclear magnetic resonance (proton NMR, hydrogen-1 NMR, or 1H NMR) is the application of nuclear magnetic resonance in NMR spectroscopy with respect to hydrogen-1 nuclei within the molecules of a substance, in order to determine the stru ...

spectrum in which all hydrogen atoms appear at a single

chemical shift In nuclear magnetic resonance (NMR) spectroscopy, the chemical shift is the resonant frequency of an atomic nucleus relative to a standard in a magnetic field. Often the position and number of chemical shifts are diagnostic of the structure of ...

of 3.38 ppm. Unlike buckminsterfullerene, dodecahedrane has no

delocalized electron In chemistry, delocalized electrons are electrons in a molecule, ion or solid metal that are not associated with a single atom or a covalent bond.IUPAC Gold Boo''delocalization''/ref> The term delocalization is general and can have slightly dif ...

s and hence has no

aromaticity In organic chemistry, aromaticity is a chemical property describing the way in which a conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibits a stabilization stronger than would be expected from conjugation alone. The e ...

History

For over 30 years, several research groups actively pursued the

total synthesis Total synthesis, a specialized area within organic chemistry, focuses on constructing complex organic compounds, especially those found in nature, using laboratory methods. It often involves synthesizing natural products from basic, commercially ...

of dodecahedrane. A review article published in 1978 described the different strategies that existed up to then. The first attempt was initiated in 1964 by R.B. Woodward with the synthesis of the compound triquinacene which was thought to be able to simply dimerize to dodecahedrane. Other groups were also in the race, for example that of Philip Eaton and Paul von Ragué Schleyer. Leo Paquette's group at

Ohio State University The Ohio State University (Ohio State or OSU) is a public university, public Land-grant university, land-grant research university in Columbus, Ohio, United States. A member of the University System of Ohio, it was founded in 1870. It is one ...

was the first to succeed, by a complex 29-step route that mostly builds the dodecahedral skeleton one ring at a time, and finally closes the last hole. In 1987, more versatile alternative synthesis route was found by the Horst Prinzbach's group. Their approach was based on the isomerization pagodane, obtained from isodrin (isomer of aldrin) as starting material i.a. through +6 photocycloaddition. Schleyer had followed a similar approach in his synthesis of

adamantane Adamantane is an organic compound with formula C10H16 or, more descriptively, (CH)4(CH2)6. Adamantane molecules can be described as the fusion of three cyclohexane rings. The molecule is both rigid and virtually stress-free. Adamantane is the mo ...

. Following that idea, joint efforts of the Prinzbach team and the Schleyer group succeeded but obtained only 8% yield for the conversion at best. In the following decade the group greatly optimized that route, so that dodecahedrane could be obtained in multi-gram quantities. The new route also made it easier to obtain derivatives with selected substitutions and unsaturated carbon-carbon bonds. Two significant developments were the discovery of σ-bishomoaromaticity and the formation of C₂₀ fullerene from highly brominated dodecahedrane species.

Synthesis

Original route

Paquette's 1982

organic synthesis Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the gen ...

takes about 29 steps with raw materials

cyclopentadiene Cyclopentadiene is an organic compound with the chemical formula, formula C5H6. It is often abbreviated CpH because the cyclopentadienyl anion is abbreviated Cp−. This colorless liquid has a strong and unpleasant odor. At room temperature, ...

(2 equivalents 10 carbon atoms), dimethyl acetylenedicarboxylate (4 carbon atoms) and allyltrimethylsilane (2 equivalents, 6 carbon atoms). In the first leg of the procedure two molecules of

1 are

coupled ''Coupled'' is an American dating game show that aired on Fox from May 17 to August 2, 2016. It was hosted by television personality, Terrence J and created by Mark Burnett, of '' Survivor'', '' The Apprentice'', '' Are You Smarter than a 5th ...

together by reaction with elemental

sodium Sodium is a chemical element; it has Symbol (chemistry), symbol Na (from Neo-Latin ) and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 element, group 1 of the peri ...

(forming the cyclopentadienyl complex) and

iodine Iodine is a chemical element; it has symbol I and atomic number 53. The heaviest of the stable halogens, it exists at standard conditions as a semi-lustrous, non-metallic solid that melts to form a deep violet liquid at , and boils to a vi ...

to dihydrofulvalene 2. Next up is a

tandem Tandem, or in tandem, is an arrangement in which two or more animals, machines, or people are lined up one behind another, all facing in the same direction. ''Tandem'' can also be used more generally to refer to any group of persons or objects w ...

Diels–Alder reaction In organic chemistry, the Diels–Alder reaction is a chemical reaction between a Conjugated system, conjugated diene and a substituted alkene, commonly termed the Diels–Alder reaction#The dienophile, dienophile, to form a substituted cyclohexe ...

with dimethyl acetylenedicarboxylate 3 with desired sequence pentadiene-acetylene-pentadiene as in symmetrical adduct 4. An equal amount of asymmetric pentadiene-pentadiene-acetylene compound (4b) is formed and discarded. : In the next step of the sequence iodine is temporarily introduced via an iodolactonization of the diacid of 4 to dilactone 5. The

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

group is cleaved next by

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical compound and the simplest aliphatic Alcohol (chemistry), alcohol, with the chemical formula (a methyl group linked to a hydroxyl group, often ab ...

to the halohydrin 6, the

alcohol Alcohol may refer to: Common uses * Alcohol (chemistry), a class of compounds * Ethanol, one of several alcohols, commonly known as alcohol in everyday life ** Alcohol (drug), intoxicant found in alcoholic beverages ** Alcoholic beverage, an alco ...

groups converted to

ketone In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...

groups in 7 by Jones oxidation and the iodine groups reduced by a zinc-copper couple in 8. : The final 6 carbon atoms are inserted in a

nucleophilic addition In organic chemistry, a nucleophilic addition (AN) reaction is an addition reaction where a chemical compound with an electrophilic double or triple bond reacts with a nucleophile, such that the double or triple bond is broken. Nucleophilic addit ...

to the ketone groups of the

carbanion In organic chemistry, a carbanion is an anion with a lone pair attached to a tervalent carbon atom. This gives the carbon atom a negative charge. Formally, a carbanion is the conjugate base of a carbon acid: : where B stands for the base (chemist ...

10 generated from allyltrimethylsilane 9 and ''n''-butyllithium. In the next step the vinyl silane 11 reacts with

peracetic acid Peracetic acid (also known as peroxyacetic acid, or Percidine) is an organic compound with the formula CH3CO3H. This peroxy acid is a colorless liquid with a characteristic acrid odor reminiscent of acetic acid. It can be highly corrosive. Perac ...

acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main compone ...

in a radical substitution to the dilactone 12 followed by an intramolecular Friedel-Crafts alkylation with

phosphorus pentoxide Phosphorus pentoxide is a chemical compound with molecular formula Phosphorus, P4Oxygen, O10 (with its common name derived from its empirical formula, P2O5). This white crystalline solid is the anhydride of phosphoric acid. It is a powerful desic ...

to diketone 13. This molecule contains all required 20 carbon atoms and is also symmetrical which facilitates the construction of the remaining 5 carbon-carbon bonds. Reduction of the

double bond In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist betw ...

s in 13 to 14 is accomplished with

hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or Saturated ...

with palladium on carbon and that of the ketone groups to alcohol groups in 15 by

sodium borohydride Sodium borohydride, also known as sodium tetrahydridoborate and sodium tetrahydroborate, is an inorganic compound with the formula (sometimes written as ). It is a white crystalline solid, usually encountered as an aqueous basic solution. Sodi ...

. Replacement of hydroxyl by

chlorine Chlorine is a chemical element; it has Symbol (chemistry), symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate between ...

in 17 via nucleophilic aliphatic substitution takes place through the dilactone 16 ( tosyl chloride). The first C–C bond forming reaction is a kind of Birch alkylation (

lithium Lithium (from , , ) is a chemical element; it has chemical symbol, symbol Li and atomic number 3. It is a soft, silvery-white alkali metal. Under standard temperature and pressure, standard conditions, it is the least dense metal and the ...

ammonia Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pu ...

) with the immediate reaction product trapped with chloromethyl phenyl ether, the other chlorine atom in 17 is simply reduced. This temporary appendix will in a later stage prevent unwanted enolization. The newly formed

group then forms another C–C bond by photochemical Norrish reaction to 19 whose alcohol group is induced to eliminate with TsOH to

alkene In organic chemistry, an alkene, or olefin, is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or at the terminal position. Terminal alkenes are also known as Alpha-olefin, α-olefins. The Internationa ...

20. : The double bond is reduced with

hydrazine Hydrazine is an inorganic compound with the chemical formula . It is a simple pnictogen hydride, and is a colourless flammable liquid with an ammonia-like odour. Hydrazine is highly hazardous unless handled in solution as, for example, hydraz ...

and sequential diisobutylaluminum hydride reduction and pyridinium chlorochromate oxidation of 21 forms the

aldehyde In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred ...

22. A second Norrish reaction then adds another C–C bond to alcohol 23 and having served its purpose the phenoxy tail is removed in several steps: a

Birch reduction The Birch reduction or Metal-Ammonia reduction is an organic reaction that is used to convert arenes to Cyclohexa-1,4-diene, 1,4-cyclohexadienes. The reaction is named after the Australian chemist Arthur Birch (organic chemist), Arthur Birch and i ...

to diol 24, oxidation with pyridinium chlorochromate to ketoaldehyde 25 and a reverse Claisen condensation to ketone 26. A third Norrish reaction produces alcohol 27 and a second

dehydration In physiology, dehydration is a lack of total body water that disrupts metabolic processes. It occurs when free water loss exceeds intake, often resulting from excessive sweating, health conditions, or inadequate consumption of water. Mild deh ...

28 and another reduction 29 at which point the synthesis is left completely without

functional group In organic chemistry, a functional group is any substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions r ...

s. The missing C-C bond is put in place by hydrogen pressurized dehydrogenation with palladium on carbon at 250 °C to dodecahedrane 30.

Pagodane route

In Prinzbach's optimized route from pagodane to dodecahedrane, the original low-yielding isomerization of parent pagodane to dodecahedrane is replaced by a longer but higher yielding sequence - which nevertheless still relies heavily on pagodane derivatives. In the scheme below, the divergence from the original happens after compound 16. : Optimized Dodecahedrane Synthesis en

Derivatives

A variety of dodecahedrane derivatives have been synthesized and reported in the literature.

Hydrogen substitution

Substitution of all 20 hydrogens by

fluorine Fluorine is a chemical element; it has Chemical symbol, symbol F and atomic number 9. It is the lightest halogen and exists at Standard temperature and pressure, standard conditions as pale yellow Diatomic molecule, diatomic gas. Fluorine is extre ...

atoms yields the relatively unstable perfluorododecahedrane C₂₀F₂₀, which was obtained in milligram quantities. Trace amounts of the analogous perchlorododecahedrane C₂₀Cl₂₀ were obtained, among other partially chlorinated derivatives, by reacting dissolved in liquid

under pressure at about 140 °C and under intense light for five days. Complete replacement by heavier

halogen The halogens () are a group in the periodic table consisting of six chemically related elements: fluorine (F), chlorine (Cl), bromine (Br), iodine (I), and the radioactive elements astatine (At) and tennessine (Ts), though some authors would ...

s seems increasingly difficult due to their larger size. Half or more of the hydrogen atoms can be substituted by

hydroxyl In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...

groups to yield

polyols In organic chemistry, a polyol is an organic compound containing multiple hydroxyl groups (). The term "polyol" can have slightly different meanings depending on whether it is used in food science or polymer chemistry. Polyols containing two, thre ...

, but the extreme compound C₂₀(OH)₂₀ remained elusive as of 2006. Amino-dodecahedranes comparable to

amantadine Amantadine, sold under the brand name Gocovri among others, is a medication used to treat dyskinesia associated with parkinsonism and influenza caused by type A influenzavirus, though its use for the latter is no longer recommended because ...

have been prepared, but were more toxic and with weaker antiviral effects. Annulated dodecahedrane structures have been proposed.

Encapsulation

Molecules whose framework forms a closed cage, like dodecahedrane and buckminsterfullerene, can encapsulate atoms and small molecules in the hollow space within. Those insertions are not chemically bonded to the caging compound, but merely mechanically trapped in it. Cross, Saunders and Prinzbach succeeded in encapsulating

helium Helium (from ) is a chemical element; it has chemical symbol, symbol He and atomic number 2. It is a colorless, odorless, non-toxic, inert gas, inert, monatomic gas and the first in the noble gas group in the periodic table. Its boiling point is ...

atoms in dodecahedrane by shooting He⁺ ions at a film of the compound. They obtained

microgram In the metric system, a microgram or microgramme is a unit of mass equal to one millionth () of a gram. The unit symbol is μg according to the International System of Units (SI); the recommended symbol in the United States and United Kingdom wh ...

quantities of (the "@" being the standard notation for encapsulation), which they described as a quite stable substance. The molecule has been described as "the world's smallest helium balloon".

References

{{reflist, colwidth=30em , refs= {{cite journal, title=Dodecahedrane , first1=Robert J., last1= Ternansky, first2= Douglas W., last2= Balogh, first3= Leo A., last3= Paquette , journal= J. Am. Chem. Soc. , date=1982 , volume=104, issue=16 , pages=4503–4504 , doi=10.1021/ja00380a040 {{cite journal , first1= Leo A. , last1=Paquette, first2= Robert J., last2= Ternansky, first3= Douglas W., last3= Balogh, first4= Gary, last4= Kentgen , year = 1983 , title = Total synthesis of dodecahedrane , journal = J. Am. Chem. Soc. , volume = 105 , issue = 16 , pages = 5446–5450 , doi =10.1021/ja00354a043 {{cite journal, title=Towards dodecahedrane, journal=

Tetrahedron In geometry, a tetrahedron (: tetrahedra or tetrahedrons), also known as a triangular pyramid, is a polyhedron composed of four triangular Face (geometry), faces, six straight Edge (geometry), edges, and four vertex (geometry), vertices. The tet ...

, volume=35, issue=19, date=1979, pages=2189–2223, first= Philip E., last= Eaton , doi=10.1016/0040-4020(79)80114-3 {{cite journal, title=Domino Diels–Alder reactions. I. Applications to the rapid construction of polyfused cyclopentanoid systems, first1=Leo A., last1=Paquette , first2=Matthew J. , last2=Wyvratt , journal= J. Am. Chem. Soc., date=1974, volume=96, issue=14, pages=4671–4673, doi=10.1021/ja00821a052 {{cite journal, title=Topologically spherical molecules. Synthesis of a pair of C₂-symmetric hexaquinane dilactones and insights into their chemical reactivity. An efficient π-mediated 1,6-dicarbonyl reduction, first1=Leo A., last1= Paquette, first2= Matthew J., last2= Wyvratt, first3= Otto, last3= Schallner, first4= Jean L., last4= Muthard, first5= William J., last5= Begley, first6= Robert M., last6= Blankenship, first7=Douglas, last7= Balogh , journal= J. Org. Chem., date=1979, volume=44, issue=21, pages=3616–3630, doi=10.1021/jo01335a003 {{cite journal, first1=Wolf-Dieter , last1=Fessner , first2=Bulusu A. R. C. , last2=Murty , first3=Horst , last3=Prinzbach , date=1987, title=The Pagodane Route to Dodecahedranes – Thermal, Reductive, and Oxidative Transformations of Pagodanes , journal= Angew. Chem. Int. Ed. Engl., volume=26 , issue=5 , pages=451–452 , doi=10.1002/anie.198704511 {{cite journal, first1=Wolf-Dieter , last1=Fessner , first2=Bulusu A. R. C. , last2=Murty , first3=Jürgen , last3=Wörth , first4=Dieter , last4=Hunkler , first5=Hans , last5=Fritz , first6=Horst , last6=Prinzbach , first7=Wolfgang D. , last7=Roth, first8=Paul von Ragué , last8=Schleyer , first9=Alan B. , last9=McEwen, first10= Wilhelm F., last10= Maier , date=1987 , title=Dodecahedranes from .1.1.1agodanes, journal= Angew. Chem. Int. Ed. Engl., volume=26 , issue=5 , pages=452–454 , doi=10.1002/anie.198704521 {{cite journal, first1=G. K. S., last1=Prakash, first2=V. V., last2=Krishnamurthy, first3=R., last3=Herges, first4=R., last4=Bau, first5=H., last5=Yuan, first6=G. A., last6=Olah, first7=W.-D., last7=Fessner, first8=H., last8=Prinzbach, title= .1.1.1 and .2.1.1agodane Dications: Frozen Two-Electron Woodward–Hoffmann Transition State Models, journal= J. Am. Chem. Soc., date=1988, volume=110, issue=23, pages=7764–7772, doi=10.1021/ja00231a029 {{cite journal, first1=Horst , last1=Prinzbach, first2= Andreas, last2= Weiler, first3= Peter , last3=Landenberger, first4= Fabian , last4=Wahl, first5= Jürgen, last5= Wörth, first6= Lawrence T. , last6=Scott, first7= Marc , last7=Gelmont, first8= Daniela, last8= Olevano, first9= Bernd von , last9=Issendorff, title=Gas-phase production and photoelectron spectroscopy of the smallest fullerene, C₂₀, journal=

Nature Nature is an inherent character or constitution, particularly of the Ecosphere (planetary), ecosphere or the universe as a whole. In this general sense nature refers to the Scientific law, laws, elements and phenomenon, phenomena of the physic ...

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External links

Paquette's dodecahedrane synthesis at SynArchive.com

2D and 3D models of dodecahedrane and cuneane assemblies

Full text of Paquette's paper
Polycyclic nonaromatic hydrocarbons Total synthesis Cyclopentanes Substances discovered in the 1980s