Bullvalene

Title: Bullvalene
CAS Registry Number: 1005-51-2
CAS Name: Tricyclo[3.3.2.02,8]deca-3,6,9-triene
Additional Names: tricyclo[3.3.2.04,6]deca-2,7,9-triene
Molecular Formula: C10H10
Molecular Weight: 130.19
Percent Composition: C 92.26%, H 7.74%
Literature References: Molecular structure is highly fluxional; spontaneously undergoes a 3-fold structurally degenerate Cope rearrangement at room temp, resulting in 10!/3 structurally equivalent geometric isomers. 1H NMR spectrum is a sharp singlet peak at high temp. Predicted as a hypothetical molecule: W. von E. Doering, W. R. Roth, Tetrahedron 19, 715 (1963). Prepn: G. Schröder, Angew. Chem. 75, 722 (1963). 1H NMR spectrum: R. Merényi et al., Ber. 97, 3150 (1964). Vapor phase structure determn: B. Andersen, A. Marstrander, Acta Chem. Scand. 25, 1271 (1971). Microwave and vibrational spectral study: W. M. Stigliani, V. W. Laurie, J. Mol. Spectrosc. 60, 188 (1976). Calorimetry study: M. Mansson, S. Sunner, J. Chem. Thermodyn. 13, 671 (1981). Review of chemistry: G. Schröder, J. F. M. Oth, Angew. Chem. Int. Ed. 6, 414-423 (1967); of discovery and characterization: A. Ault, J. Chem. Educ. 78, 924-927 (2001).
Properties: mp 96°.
Melting point: mp 96°
Bumadizon Bumetanide Bunaftine Bunamidine Bunamiodyl Sodium

Bullvalene
Bullvalene.svg Bullvalene-from-xtal-3D-balls.png
Identifiers
CAS number 1005-51-2 YesY
PubChem 136796
ChemSpider 120549 YesY
Jmol-3D images Image 1
Properties
Molecular formula C10H10
Molar mass 130.19 g/mol
Melting point 96°C
Boiling point decomposition at about 400°C
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Bullvalene is a hydrocarbon with the chemical formula C10H10 with the unusual property that the chemical bonds making up the molecule are constantly rearranging as in fluxional molecules. For this reason bullvalene is extensively studied in organic chemistry.