Methylenecyclopropane

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Methylenecyclopropane
IUPAC name

methylenecyclopropane

Identifiers
CAS number 6142-73-0
PubChem 80245
ChemSpider 72487
Jmol-3D images Image 1
Properties
Molecular formula C4H6
Molar mass 54.09
Density 0.8 g/cm3
Boiling point 9-12 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Methylenecyclopropane is an organic compound with the formula (CH2)2CCH2. It is a colourless easily condensed gas that is used as a reagent in organic synthesis.

Synthesis

Methylenecyclopropane can be synthesised via an intramolecular cyclisation reaction, using β-halo alkenes and a strong base such as sodium amide.[1]

Reactions

Being a strained and unsaturated molecule methylenecyclopropane undergoes many reactions, especially in the presence of metal catalysts.[2] For example methylenecyclopropanes can be converted to cyclobutenes in the presence of a Platinum catalyst.[3] This can be considered similar to the ring expansion seen in vinylcyclopropane rearrangements

Substituted methylenecyclopropanes can also be involved in trimethylenemethane cycloaddition reactions.

See also

References

  1. ↑ Salaun, J. R.; Champion, J.; Conia, J. M. (1977), "Cyclobutanone from methylenecyclopropane via oxaspiropentane", Org. Synth. 57: 36 ; Coll. Vol. 6: 320 
  2. ↑ Nakamura, I.; Yamamoto, Y. (2002). "Transition Metal-Catalyzed Reactions of Methylenecyclopropanes". Advanced Synthesis and Catalysis 344 (2): 111–129. doi:10.1002/1615-4169(200202)344:2<111::AID-ADSC111>3.0.CO;2-0. 
  3. ↑ PtCl2-Catalyzed Rearrangement of Methylenecyclopropanes Alois Fürstner and Christophe Aïssa J. Am. Chem. Soc.; 2006; 128(19) pp 6306 -6307; Abstract
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