Cyclobutene

Cyclobutene
Names
	Preferred IUPAC name Cyclobutene
Identifiers
CAS Number	822-35-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:51206 ;
ChemSpider	63164 ;
ECHA InfoCard	100.011.360
EC Number	212-496-8;
PubChem CID	69972;
CompTox Dashboard (EPA)	DTXSID60231616 ;
	InChI InChI=1S/C4H6/c1-2-4-3-1/h1-2H,3-4H2 Key: CFBGXYDUODCMNS-UHFFFAOYSA-N ; InChI=1/C4H6/c1-2-4-3-1/h1-2H,3-4H2 Key: CFBGXYDUODCMNS-UHFFFAOYAN;
	SMILES C\1=C\CC/1;
Properties
Chemical formula	C4H6
Molar mass	54.092 g·mol−1
Appearance	Colorless gas
Density	0.733 g/cm3
Boiling point	2 °C (36 °F; 275 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). verify (what is ?) Infobox references

Cyclobutene is an organic compound with the chemical formula C₄H₆. It is a cycloalkene. It is a colorless gas that easily condenses. It is of interest in research but currently has no practical applications. A modern synthesis involves the 2-step dehydration of cyclobutanol.^[1] The compound was first prepared by thermolysis of the ammonium salt [C₄H₇N(CH₃)₃OH (cyclobutyltrimethylammonium hydroxide).^[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]

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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[OrgSynth-1] J. Salaün; A. Fadel (1986). "Cyclobutene". Org. Synth. 64: 50. doi:10.15227/orgsyn.064.0050.

[2] Willstätter, R.; von Schmaedel, W. (1905). "Ueber einige Derivate des Cyclobutans". Chem. Ber. 38 (2): 1992–1999. doi:10.1002/cber.190503802130.

[3] 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.

[1]

[2]

[3]

v t e Cycloalkenes
Alkenes	Cyclopropene Cyclobutene Cyclopentene Cyclohexene Cycloheptene Cyclooctene Cyclononene Cyclodecene
Dienes	Cyclobutadiene Cyclopentadiene Cyclohexadiene 1,3-Cyclohexadiene 1,4-Cyclohexadiene Cycloheptadiene 1,3-Cycloheptadiene 1,4-Cycloheptadiene Cyclooctadiene 1,5-Cyclooctadiene
Trienes	Benzene Cycloheptatriene
Tetraenes	Cyclooctatetraene Cyclononatetraene

See also

References