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Cyclobutene

From Wikipedia, the free encyclopedia
Cyclobutene
Names
Preferred IUPAC name
Cyclobutene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard100.011.360Edit this at Wikidata
EC Number
  • 212-496-8
  • InChI=1S/C4H6/c1-2-4-3-1/h1-2H,3-4H2 checkY
    Key: CFBGXYDUODCMNS-UHFFFAOYSA-N checkY
  • InChI=1/C4H6/c1-2-4-3-1/h1-2H,3-4H2
    Key: CFBGXYDUODCMNS-UHFFFAOYAN
  • C\1=C\CC/1
Properties
C4H6
Molar mass54.092 g·mol−1
AppearanceColorless gas
Density0.733 g/cm3
Boiling point2 °C (36 °F; 275 K)[1]
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Cyclobutene is anorganic compound with thechemical formulaC4H6. It is acycloalkene. It is a colorless gas that easilycondenses. It is of interest in research but currently has no practical applications. A modern synthesis involves the 2-stepdehydration ofcyclobutanol.[1] The compound was first prepared bythermolysis of theammonium salt[C4H7N(CH3)3]OH (cyclobutyltrimethylammonium hydroxide).[2]

Cyclobutene thermallyisomerizes to1,3-butadiene. This stronglyexothermic reaction reflects the dominance ofring strain. In contrast, the correspondingequilibrium forhexafluorocyclobutene disfavorshexafluorobutadiene.[3]

See also

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References

[edit]
  1. ^abJ. 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.
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Alkenes
Dienes
Trienes
Tetraenes
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