Methylenecyclopropene

Methylenecyclopropene
Names
Preferred IUPAC name
3-Methylidenecycloprop-1-ene
Other names
3-Methylenecyclopropene
Triafulvene
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C4H4/c1-4-2-3-4/h2-3H,1H2 ☒N
    Key: GOSMMPKSWSOPRZ-UHFFFAOYSA-N ☒N
  • InChI=1/C4H4/c1-4-2-3-4/h2-3H,1H2
    Key: GOSMMPKSWSOPRZ-UHFFFAOYAD
  • C=C1C=C1
Properties
C4H4
Molar mass 52.076 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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3-Methylenecyclopropene, also called methylenecyclopropene or triafulvene, is a hydrocarbon with chemical formula C4H4. It is a colourless gas that polymerizes readily as a liquid or in solution but is stable as a gas.[1] This highly strained and reactive molecule was synthesized and characterized for the first time in 1984, and has been the subject of considerable experimental and theoretical interest. It is an example of a cross-conjugated alkene, being composed of cyclopropene with an exocyclic double bond attached.

  1. ^ W. E. Billups , Long Jin Lin , Edward W. Casserly "Synthesis of Methylenecyclopropene" J. Am. Chem. Soc., 1984, volume 106, pp 3698–3699. doi:10.1021/ja00324a064