Tetrahedrane
Tetrahedrane (Tricyclo [1.1.0.0 2,4 ] butane) is a hypothetical cycloalkane with the empirical formula C 4 H 4 , the carbon atoms of which are in the corners of a tetrahedron . Since the tetrahedron is a platonic solid , tetrahedrane is also called a platonic molecule and belongs to the platonic hydrocarbons . One also speaks of a cage connection , since it is a geometric object with an interior.
Tetrahedrane itself is not unbound or does not exist naturally. In the tetrahedran molecule there are bond angles of 60 ° between the four carbon atoms, which deviate strongly from the ideal tetrahedron angle of 109.5 ° and cause tension in the molecule ( Baeyer tension ). So far (2017) the synthesis of tetrahedrane has not yet been successful.
tert -butyl-tetrahedrane
However, managed Günther Maier the carbon backbone with and staff at the University of Marburg tert -butyl - substituents build. These spatially extended groups provide additional stability through a “corset effect”.
For the synthesis of this Tetrahedranderivats is tetra- tert -butylcyclopentadienon exposed. The result tetra- tert -butyltricyclopentanon (1,3,4,5-tetra- tert -butyl-tricyclo [2.1.0.0 3,5 ] pentan-2-one), which upon further exposure carbon monoxide cleaves and tetra- tert -butyltetrahedran (1,2,3,4-tetra- tert -butyl-tricyclo [1.1.0.0 2,4 ] butane) forms, with the tetra- tert -butylcyclobutadien is in a thermally induced equilibrium.
literature
- D. Pappusch: Studies on the unsubstituted tetrahedrane and tetrakis (trimethylsilyl) tetrahedrane , dissertation, University of Gießen 2003. urn : nbn: de: hebis: 26-opus-12774
Web links
Individual evidence
- ↑ External identifiers of or database links for tetra-tert-butyltetrahedran : CAS number: 66809-06-1, PubChem : 144194 , ChemSpider : 127202 , Wikidata : Q27116881 .
- ↑ G. Maier, S. Pfriem, U. Schäfer, R. Matusch: Tetra-tert-butyltetrahedrane in Angew. Chem. Int. Ed. 17, No. 7, 1978, pp. 520-521, doi : 10.1002 / anie.197805201 .