Housane

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Housane
Housane.svg
Housane.png
Names
Preferred IUPAC name
Bicyclo[2.1.0]pentane
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C5H8/c1-2-5-3-4(1)5/h4-5H,1-3H2
    Key: MHLPKAGDPWUOOT-UHFFFAOYSA-N
  • InChI=1/C5H8/c1-2-5-3-4(1)5/h4-5H,1-3H2
    Key: MHLPKAGDPWUOOT-UHFFFAOYAN
  • C1C2CCC12
Properties
C5H8
Molar mass 68.119 g·mol−1
Appearancecolorless liquid
Boiling point 45.5 ′C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Housane or bicyclo[2.1.0]pentane is a saturated cycloalkane with the formula C5H8. It is a colorless, volatile liquid at room temperature. It was named "housane" because of its shape, which resembles a simple drawing of a house. Structurally, the molecule consists of cyclopropane fused to cyclobutane. The synthesis of molecules containing multiple strained rings, such as housane, is a traditional endeavor in synthetic organic chemistry.

Contents

Preparation

The first synthesis of housane was reported by Criegee in 1957, where housane was obtained from the pyrolysis of 2,3-diazabicyclo[2.2.1]hept-2-ene. [1]

Synthesis Bicyclo(2.1.0)pentane.svg

Housane can be prepared in several steps starting with cyclopentadiene. Other methods include photolysis of 2,3-diazabicyclo[2.2.1]hept-2-ene, pyrolysis of N-Phenyl-2-oxo-3-azabicyclo[2.2.1]heptane, and addition of methylene to cyclobutene. [2]

Structure and properties

Housane is easily attacked by bromine or iodine. In the presence of a platinum catalyst at room temperature, it is hydrogenated into cyclopentane. Reaction with hydrogen bromide at lower temperatures affords bromocyclopentane. Housane also reacts with lead tetraacetate, forming cis-1,3-diacetoxycyclopentane among other products. [1]

Reactions Bicyclo(2.1.0)pentane.svg

Housane is thermally quite stable, isomerizing to cyclopentene at 330 °C. [1]

See also

References

  1. 1 2 3 Criegee, Rudolf; Rimmelin, Annemarie (1957). "Darstellung und Eigenschaften von Bicyclo‐[0.1.2]‐Pentan" [Preparation and Properties of Bicyclo-[0.1.2]-pentane]. Chemische Berichte. 90 (3): 414–417. doi:10.1002/cber.19570900319. ISSN   0009-2940.
  2. ↑ P. G. Gassman, K. T. Mansfield "Bicyclo[2.1.0]pentane" Org. Synth. 1969, volume 49, pp. 1. doi : 10.15227/orgsyn.049.0001
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