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Methylenecyclopropane

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Organic compound, (CH₂)₂C=CH₂
Methylenecyclopropane
Names
Preferred IUPAC name Methylidenecyclopropane
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.025.584 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H6/c1-4-2-3-4/h1-3H2Key: XSGHLZBESSREDT-UHFFFAOYSA-N
  • InChI=1/C4H6/c1-4-2-3-4/h1-3H2Key: XSGHLZBESSREDT-UHFFFAOYAB
SMILES
  • C=C1CC1
Properties
Chemical formula C4H6
Molar mass 54.09
Density 0.8 g/cm
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 , 100 kPa). Infobox references
Chemical compound

Methylenecyclopropane is an organic compound with the formula (CH2)2C=CH2. It is a hydrocarbon which, as the name suggests, is derived from the addition of a methylene (=CH2) substituent to a cyclopropane ring. It is a colourless, easily condensed gas that is used as a reagent in organic synthesis.

Synthesis

Methylenecyclopropane can be synthesized via an intramolecular cyclisation reaction from methallyl chloride by treatment with a strong base such sodium amide—sodium tert-butoxide (yield 43%) or sodium bis(trimethylsilyl)amide with further treatment by sodium tert-butoxide (yield 72%). Sodium tert-butoxide is used to isomerize byproduct 1-methylcyclopropene into methylenecyclopropane.

Reactions

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

Methylene cyclopropane isomerization

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. Binger, Paul; Brinkmann, Axel; Wedemann, Petra (2002). "Highly Efficient Synthesis of Methylenecyclopropane". Synthesis (10): 1344–1346. doi:10.1055/s-2002-33122. ISSN 0039-7881.
  3. 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.
  4. 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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