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Concept
Tetrahedrane
Summary
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 been prepared. In a more general sense, the term tetrahedranes is used to describe a class of molecules and ions with related structure, e.g. white phosphorus.
In 1978, Günther Maier prepared tetra-tert-butyl-tetrahedrane. These bulky substituents envelop the tetrahedrane core. Maier suggested that bonds in the core are prevented from breaking because this would force the substituents closer together (corset effect) resulting in Van der Waals strain. Tetrahedrane is one of the possible platonic hydrocarbons and has the IUPAC name tricyclo[1.1.0.02,4]butane.
Unsubstituted tetrahedrane () remains elusive, although it is predicted to be kinetically stable. One strategy that has been explored (but thus far failed) is reaction of propene with atomic carbon. Locking away a tetrahedrane molecule inside a fullerene has only been attempted in silico. Due to its bond strain and stoichiometry, tetranitrotetrahedrane has potential as a high-performance energetic material (explosive). Some properties have been calculated based on quantum chemical methods.
This compound was first synthesised starting from a cycloaddition of an alkyne with t-Bu substituted maleic anhydride, followed by rearrangement with carbon dioxide expulsion to a cyclopentadienone and its bromination, followed by addition of the fourth t-Bu group. Photochemical cheletropic elimination of carbon monoxide of the cyclopentadienone gives the target. Heating tetra-tert-butyltetrahedrane gives tetra-tert-butylcyclobutadiene. Though the synthesis appears short and simple, by Maier's own account, it took several years of careful observation and optimization to develop the correct conditions for the challenging reactions to take place.
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