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)3]OH (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]

See also

References

  1. ^ a b 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.