Methylenecyclopropane

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.

Methylenecyclopropane
Names
IUPAC name
methylidenecyclopropane
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.025.584
Properties
C4H6
Molar mass 54.09
Density 0.8 g/cm3
Boiling point 9 to 12 °C (48 to 54 °F; 282 to 285 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Synthesis

Methylenecyclopropane can be synthesised via an intramolecular cyclisation reaction from methallyl chloride by treatment with 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". Organic Syntheses. 57: 36. doi:10.15227/orgsyn.057.0036.
  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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