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 hydrophobic, and their odors are usually weak or ...

with formula , whose

carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent—its atom making four electrons available to form covalent chemical bonds. It belongs to group 14 of the periodic table. Carbon ma ...

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

dodecahedron In geometry, a dodecahedron (Greek , from ''dōdeka'' "twelve" + ''hédra'' "base", "seat" or "face") or duodecahedron is any polyhedron with twelve flat faces. The most familiar dodecahedron is the regular dodecahedron with regular pentagon ...

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

hydrogen Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-to ...

atom. This compound is one of the three possible

Platonic hydrocarbons In organic chemistry, a Platonic hydrocarbon is a hydrocarbon ( molecule) whose structure matches one of the five Platonic solids, with carbon atoms replacing its vertices, carbon–carbon bonds replacing its edges, and hydrogen atoms as nee ...

, the other two being

cubane Cubane () 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 an ...

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 as of 2021. However, a number of derivatives have b ...

. Dodecahedrane does not occur in nature and has no significant uses. It was synthesized by

Leo Paquette Leo Armand Paquette ( – January 21, 2019) was an American organic chemist. Biography He was born on July 15, 1934 to parents Armand and Clarice with roots in Quebec (great-grandfather Edmund was born in Contrecoeur, Quebec) and he received h ...

in 1982, primarily for the "aesthetically pleasing

symmetry Symmetry (from grc, συμμετρία "agreement in dimensions, due proportion, arrangement") in everyday language refers to a sense of harmonious and beautiful proportion and balance. In mathematics, "symmetry" has a more precise definiti ...

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 held together by attractive forces known as chemical bonds; depending on context, the term may or may not include ions which satisfy this criterion. In quantum physics, organic chemistry, and b ...

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 C60. It has a cage-like fused-ring structure (truncated icosahedron) made of twenty hexagons and twelve pentagons, and resembles a soccer ball. Each of its 60 carbon atoms is bonded ...

(), 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 Bromine is a chemical element with the symbol Br and atomic number 35. It is the third-lightest element in group 17 of the periodic table (halogens) and is a volatile red-brown liquid at room temperature that evaporates readily to form a simila ...

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 (from the Greek πέντε ''pente'' meaning ''five'' and γωνία ''gonia'' meaning ''angle'') is any five-sided polygon or 5-gon. The sum of the internal angles in a simple pentagon is 540°. A pentagon may be simpl ...

. That value is quite close to the 109.5°

central angle A central angle is an angle whose apex (vertex) is the center O of a circle and whose legs (sides) are radii intersecting the circle in two distinct points A and B. Central angles are subtended by an arc between those two points, and the arc le ...

of a

regular tetrahedron In geometry, a tetrahedron (plural: tetrahedra or tetrahedrons), also known as a triangular pyramid, is a polyhedron composed of four triangular faces, six straight edges, and four vertex corners. The tetrahedron is the simplest of all th ...

—the ideal angle between the bonds on an atom that has (sp³ hybridisation. As a result, there is minimal

angle strain In organic chemistry, ring strain is a type of instability that exists when bonds in a molecule form angles that are abnormal. Strain is most commonly discussed for small rings such as cyclopropanes and cyclobutanes, whose internal angles are ...

. However, the molecule has significant levels of torsional strain as a result of the

eclipsed conformation In chemistry an eclipsed conformation is a conformation in which two substituents X and Y on adjacent atoms A, B are in closest proximity, implying that the torsion angle X–A–B–Y is 0°. Such a conformation can exist in any open chain ...

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 struct ...

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 o ...

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 chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to satur ...

History

For over 30 years, several research groups actively pursued the

total synthesis Total synthesis is the complete chemical synthesis of a complex molecule, often a natural product, from simple, commercially-available precursors. It usually refers to a process not involving the aid of biological processes, which distinguishes i ...

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 Philip E. Eaton (born 1936) is a Professor Emeritus of Chemistry at the University of Chicago. He and his fellow researchers were the first to synthesize the "impossible" cubane molecule in 1964.P. Eaton and T. W. Cole, The Cubane System, J. Am. ...

and

Paul von Ragué Schleyer Paul von Ragué Schleyer (February 27, 1930 – November 21, 2014) was an American physical organic chemist whose research is cited with great frequency. A 1997 survey indicated that Dr. Schleyer was, at the time, the world's third most cited chem ...

. Leo Paquette's group at

Ohio State University The Ohio State University, commonly called Ohio State or OSU, is a public land-grant research university in Columbus, Ohio. A member of the University System of Ohio, it has been ranked by major institutional rankings among the best pub ...

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 Pagodane is an organic compound with formula whose carbon skeleton was said to resemble a pagoda, hence the name. It is a polycyclic hydrocarbon whose molecule has the ''D''2''h'' point symmetry group. The compound is a highly crystalline soli ...

, obtained from

isodrin Isodrin may refer to either of two chemical compounds: * Isodrin, an organochlorine insecticide which is an isomer of aldrin * Pholedrine Pholedrine (Paredrinol, Pulsotyl, Veritol), also known as 4-hydroxy-''N''-methylamphetamine (4-HMA), 4-hy ...

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 a 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 ...

. 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 significative 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 special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...

takes about 29 steps with raw materials

cyclopentadiene Cyclopentadiene is an organic compound with the formula C5H6.LeRoy H. Scharpen and Victor W. Laurie (1965): "Structure of cyclopentadiene". ''The Journal of Chemical Physics'', volume 43, issue 8, pages 2765-2766. It is often abbreviated CpH beca ...

(2 equivalents 10 carbon atoms),

dimethyl acetylenedicarboxylate Dimethyl acetylenedicarboxylate (DMAD) is an organic compound with the formula CH3O2CC2CO2CH3. It is a di-ester in which the ester groups are conjugated with a C-C triple bond. As such, the molecule is highly electrophilic, and is widely employed ...

(4 carbon atoms) and

allyltrimethylsilane Allyltrimethylsilane is the organosilicon compound with the formula (CH3)3SiCH2CH=CH2. The molecule consists of the trimethylsilyl group attached to allyl group. This colorless liquid is used in organic synthesis Organic synthesis is a spec ...

(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 G ...

together by reaction with elemental

sodium Sodium is a chemical element with the symbol Na (from Latin ''natrium'') and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 of the periodic table. Its only stable ...

(forming the

cyclopentadienyl complex A cyclopentadienyl complex is a coordination complex of a metal and cyclopentadienyl groups (, abbreviated as Cp−). Cyclopentadienyl ligands almost invariably bind to metals as a pentahapto (''η''5-) bonding mode. The metal–cyclopentadien ...

) and

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

to dihydrofulvalene 2. Next up is a

tandem Tandem, or in tandem, is an arrangement in which a team of machines, animals or people are lined up one behind another, all facing in the same direction. The original use of the term in English was in ''tandem harness'', which is used for two ...

Diels–Alder reaction In organic chemistry, the Diels–Alder reaction is a chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene derivative. It is the prototypical example of a peric ...

with

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 oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ...

group is cleaved next by

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is ...

to the

halohydrin In organic chemistry a halohydrin (also a haloalcohol or β-halo alcohol) is a functional group in which a halogen and a hydroxyl are bonded to adjacent carbon atoms, which otherwise bear only hydrogen or hydrocarbyl groups (e.g. 2-chloroethanol ...

6, the

alcohol Alcohol most commonly refers to: * Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom * Alcohol (drug), an intoxicant found in alcoholic drinks Alcohol may also refer to: Chemicals * Ethanol, one of sev ...

groups converted to

ketone In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double b ...

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 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 additions d ...

to the ketone groups of the

carbanion In organic chemistry, a carbanion is an anion in which carbon is trivalent (forms three bonds) and bears a formal negative charge (in at least one significant resonance form). Formally, a carbanion is the conjugate base of a carbon acid: :R3 ...

10 generated from

9 and ''n''-butyllithium. In the next step the

vinyl silane Vinylsilane refers to an organosilicon compound with chemical formula CH2=CHSiH3. It is a derivative of silane (SiH4). The compound, which is a colorless gas, is mainly of theoretical interest. Substituted vinylsilanes More commonly used than th ...

11 reacts with

peracetic acid Peracetic acid (also known as peroxyacetic acid, or PAA) 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. Peracetic ...

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 componen ...

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 P4 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 desiccant and dehydra ...

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 betwee ...

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 reduce or saturate organic ...

with

palladium on carbon Palladium on carbon, often referred to as Pd/C, is a form of palladium used as a catalyst. The metal is supported on activated carbon to maximize its surface area and activity. Uses Hydrogenation Palladium on carbon is used for catalytic hydrog ...

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 Na BH4. This white solid, usually encountered as an aqueous basic solution, is a reducing agent that finds applica ...

. Replacement of hydroxyl by

chlorine Chlorine is a chemical element with the 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 them. Chlorine i ...

in 17 via

nucleophilic aliphatic substitution In chemistry, a nucleophilic substitution is a class of chemical reactions in which an electron-rich chemical species (known as a nucleophile) replaces a functional group within another electron-deficient molecule (known as the electrophile). Th ...

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

lithium Lithium (from el, λίθος, lithos, lit=stone) is a chemical element with the symbol Li and atomic number 3. It is a soft, silvery-white alkali metal. Under standard conditions, it is the least dense metal and the least dense soli ...

ammonia Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogenous ...

) 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 In organic chemistry, alkenols (shortened to enols) are a type of reactive structure or intermediate in organic chemistry that is represented as an alkene (olefin) with a hydroxyl group attached to one end of the alkene double bond (). The ter ...

. The newly formed

group then forms another C–C bond by

photochemical Photochemistry is the branch of chemistry concerned with the chemical effects of light. Generally, this term is used to describe a chemical reaction caused by absorption of ultraviolet (wavelength from 100 to 400 nm), visible light (400–7 ...

Norrish reaction A Norrish reaction in organic chemistry is a photochemical reaction taking place with ketones and aldehydes. Such reactions are subdivided into Norrish type I reactions and Norrish type II reactions. The reaction is named after Ronald George Wreyfor ...

to 19 whose alcohol group is induced to eliminate with

TsOH ''p''-Toluenesulfonic acid (PTSA or ''p''TsOH) or tosylic acid (TsOH) is an organic compound with the formula CH3 C6H4 SO3H. It is a white extremely hygroscopic solid that is soluble in water, alcohols, and other polar organic solvents. The CH3 ...

alkene In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic ...

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 toxic unless handled in solution as, for example, hydrazine ...

and sequential

diisobutylaluminum hydride Diisobutylaluminium hydride (DIBALH, DIBAL, DIBAL-H or DIBAH) is a reducing agent with the formula (''i''-Bu2AlH)2, where ''i''-Bu represents isobutyl (-CH2CH(CH3)2). This organoaluminium compound is a reagent in organic synthesis. Properties Lik ...

reduction and pyridinium chlorochromate oxidation of 21 forms the

aldehyde In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl gro ...

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 is an organic reaction that is used to convert arenes to cyclohexadienes. The reaction is named after the Australian chemist Arthur Birch and involves the organic reduction of aromatic rings in an amine solvent (traditionally ...

to diol 24, oxidation with pyridinium chlorochromate to ketoaldehyde 25 and a reverse

Claisen condensation The Claisen condensation is a carbon–carbon bond forming reaction that occurs between two esters or one ester and another carbonyl compound in the presence of a strong base, resulting in a β-keto ester or a β-diketone. It is named after Ra ...

to ketone 26. A third Norrish reaction produces alcohol 27 and a second

dehydration In physiology, dehydration is a lack of total body water, with an accompanying disruption of metabolic processes. It occurs when free water loss exceeds free water intake, usually due to exercise, disease, or high environmental temperature. Mil ...

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

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

s. The missing C-C bond is put in place by hydrogen pressurized

dehydrogenation In chemistry, dehydrogenation is a chemical reaction that involves the removal of hydrogen, usually from an organic molecule. It is the reverse of hydrogenation. Dehydrogenation is important, both as a useful reaction and a serious problem. A ...

with

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 with the symbol F and atomic number 9. It is the lightest halogen and exists at standard conditions as a highly toxic, pale yellow diatomic gas. As the most electronegative reactive element, it is extremely reactiv ...

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 five or six chemically related elements: fluorine (F), chlorine (Cl), bromine (Br), iodine (I), astatine (At), and tennessine (Ts). In the modern IUPAC nomenclature, this grou ...

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 hydrox ...

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, thr ...

, 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 due to wid ...

have been prepared, but were more toxic and with weaker antiviral effects. Annelated 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 el, ἥλιος, helios, lit=sun) is a chemical element with the symbol He and atomic number 2. It is a colorless, odorless, tasteless, non-toxic, inert, monatomic gas and the first in the noble gas group in the periodic ta ...

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 whe ...

quantities of He@ (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 A gas balloon is a balloon that rises and floats in the air because it is filled with a gas lighter than air (such as helium or hydrogen). When not in flight, it is tethered to prevent it from flying away and is sealed at the bottom to prevent t ...

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=

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Tetrahedron In geometry, a tetrahedron (plural: tetrahedra or tetrahedrons), also known as a triangular pyramid, is a polyhedron composed of four triangular faces, six straight edges, and four vertex corners. The tetrahedron is the simplest of all ...

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Nature Nature, in the broadest sense, is the physical world or universe. "Nature" can refer to the phenomena of the physical world, and also to life in general. The study of nature is a large, if not the only, part of science. Although humans are ...

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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