Cyclobutene
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| Preferred IUPAC name
Cyclobutene | |||
| Identifiers | |||
3D model (JSmol)
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| ChemSpider | |||
| ECHA InfoCard | 100.011.360 | ||
| EC Number |
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |||
| C4H6 | |||
| Molar mass | 54.09 g/mol | ||
| Density | 0.733 g/cm3 | ||
| Boiling point | 2 °C (36 °F; 275 K)[1] | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Cyclobutene is a cycloalkene. It is of interest in research but currently has no practical applications. It is a colorless easily condensed gas. A modern synthesis involves the 2-step dehydration of cyclobutanol.[1] The compound was first prepared by thermolysis of the ammonium salt [C4H7NMe3]OH.[2]
Cyclobutene thermally isomerizes to 1,3-butadiene. This strongly exothermic reaction reflects the dominance of ring strain. In contrast, the corresponding equilibrium for hexafluorocyclobutene disfavors hexafluorobutadiene.[3]
See also
References
- ^ a b J. Salaün; A. Fadel (1986). "Cyclobutene". Org. Synth. 64: 50. doi:10.15227/orgsyn.064.0050.
- ^ Willstätter, R.; von Schmaedel, W. (1905). "Ueber einige Derivate des Cyclobutans". Chem. Ber. 38 (2): 1992–1999. doi:10.1002/cber.190503802130.
- ^ David M. Lemal; Xudong Chen (2005). "Fluorinated Cyclobutanes and Their Derivatives". In Zvi Rappoport; Joel F. Liebman (eds.). The Chemistry of Cyclobutanes. PATAI'S Chemistry of Functional Groups. pp. 955–1029. doi:10.1002/0470864028.ch21. ISBN 0470864001.
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