Housane

Housane  |  |

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Names
Preferred IUPAC name

Bicyclo[2.1.0]pentane

Identifiers

CAS Number

* 185-94-4

3D model (JSmol)

* Interactive image

ChemSpider |

* 8747

PubChem CID

* 9101

InChI

* 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

SMILES

* C1C2CCC12

Properties

Chemical formula

| C5H8
Molar mass | 68.119 g·mol−1
Appearance  | colorless 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).

Infobox references

Tracking categories (test):

* PairSizeSet

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. 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.

## 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]

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

The two rings are fused in a cis configuration—this meso compound formally has (1R,4S) absolute stereochemistry. The small size of the two rings prevents the trans isomer from existing, so the stereochemistry is not usually mentioned when discussing this structure.

Housane is easily attacked by bromine or iodine. In the presence of a platinum catalyst at room temperature, it is hydrogenated to 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]

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

## References

1. ↑ 1.0 1.1 1.2 Criegee, Rudolf; Rimmelin, Annemarie (1957). "Darstellung und Eigenschaften von Bicyclo‐[0.1.2‐Pentan"] (in en). Chemische Berichte 90 (3): 414–417. doi:10.1002/cber.19570900319. ISSN 0009-2940. https://onlinelibrary.wiley.com/doi/10.1002/cber.19570900319.
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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Hydrocarbons

Saturated
aliphatic
hydrocarbons|

| Alkanes
CnH2n \+ 2|

| Linear alkanes|

* Methane
* Ethane
* Propane
* Butane
* Pentane
* Hexane
* Heptane
* Octane
* Nonane
* Decane

|

Branched alkanes|

* Isobutane
* Isopentane
* 3-Methylpentane
* Neopentane
* Isohexane
* Isoheptane
* Isooctane
* Isononane
* Isodecane

Cycloalkanes|

* Cyclopropane
* Cyclobutane
* Cyclopentane
* Cyclohexane
* Cycloheptane
* Cyclooctane
* Cyclononane
* Cyclodecane

Alkylcycloalkanes|

* Methylcyclopropane
* Methylcyclobutane
* Methylcyclopentane
* Methylcyclohexane
* Isopropylcyclohexane

Bicycloalkanes|

* Housane (bicyclo[2.1.0]pentane)
* Norbornane (bicyclo[2.2.1]heptane)
* Decalin (bicyclo[4.4.0]decane)

Polycycloalkanes|

* Adamantane
* Diamondoid
* Perhydrophenanthrene
* Sterane
* Cubane
* Prismane
* Dodecahedrane
* Basketane
* Churchane
* Pagodane
* Twistane

Other|

* Spiroalkanes

Unsaturated
aliphatic
hydrocarbons|

| Alkenes
CnH2n|

| Linear alkenes|

* Ethene
* Propene
* Butene
* Pentene
* Hexene
* Heptene
* Octene
* Nonene
* Decene

|

Branched alkenes|

* Isobutene
* Isopentene
* Isohexene
* Isoheptene
* Isooctene
* Isononene
* Isodecene

Alkynes
CnH2n − 2|

| Linear alkynes|

* Ethyne
* Propyne
* Butyne
* Pentyne
* Hexyne
* Heptyne
* Octyne
* Nonyne
* Decyne

|

Branched alkynes|

* Isopentyne
* Isohexyne
* Isoheptyne
* Isooctyne
* Isononyne
* Isodecyne

Cycloalkenes|

* Cyclopropene
* Cyclobutene
* Cyclopentene
* Cyclohexene
* Cycloheptene
* Cyclooctene
* Cyclononene
* Cyclodecene

Alkylcycloalkenes|

* Methylcyclopropene
* Methylcyclobutene
* Methylcyclopentene
* Methylcyclohexene
* Isopropylcyclohexene

Bicycloalkenes|

* Norbornene

Cycloalkynes|

* Cyclopropyne
* Cyclobutyne
* Cyclopentyne
* Cyclohexyne
* Cycloheptyne
* Cycloctyne
* Cyclononyne
* Cyclodecyne

Dienes|

* Propadiene
* Butadiene
* Pentadiene
* Hexadiene
* Heptadiene
* Octadiene
* Nonadiene
* Decadiene

Other|

* Alkatriene
* Alkadiyne
* Cumulene
* Cyclooctatetraene
* Cyclododecatriene
* Enyne

Aromatic
hydrocarbons|

| PAHs|

| Acenes|

* Naphthalene
* Anthracene
* Tetracene
* Pentacene
* Hexacene
* Heptacene

|

Other|

* Azulene
* Fluorene
* Helicenes
* Circulenes
* Butalene
* Phenanthrene
* Chrysene
* Pyrene
* Corannulene
* Kekulene

Alkylbenzenes|

* Toluene
* Xylene
* Ethylbenzene
* Cumene
* Styrene
* Mesitylene
* Pseudocumene
* Hemellitene
* Cymene
* Hexamethylbenzene

Other|

* Benzene
* Cyclopropenylidene

Other|

* Annulenes
* Annulynes
* Alicyclic compounds
* Petroleum jelly

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