Concept
Dodecahedrane is a chemical compound, a hydrocarbon with formula , whose carbon atoms are arranged as the vertices (corners) of a regular dodecahedron. Each carbon is bound to three neighbouring carbon atoms and to a hydrogen atom. This compound is one of the three possible Platonic hydrocarbons, the other two being cubane and tetrahedrane. 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 of the dodecahedral framework". For many years, dodecahedrane was the simplest real carbon-based molecule with full icosahedral symmetry. Buckminsterfullerene (), 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. The angle between the C-C bonds in each carbon atom is 108°, which is the angle between adjacent sides of a regular pentagon. That value is quite close to the 109.5° central angle of a regular tetrahedron—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 (Ih) symmetry, as evidenced by its proton NMR spectrum in which all hydrogen atoms appear at a single chemical shift of 3.38 ppm. Unlike buckminsterfullerene, dodecahedrane has no delocalized electrons and hence has no aromaticity. For over 30 years, several research groups actively pursued the total synthesis 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.