Iceane

Names

IUPAC name

Tetracyclo[5.3.1.1^2,60^4,9]dodecane

Other names

Wurtzitane

Identifiers

CAS Registry Number

53283-19-5^Y

ChemSpider

26333278^N

InChI

InChI=1S/C12H18/c1-7-2-11-3-8(1)10-4-9(7)5-12(11)6-10/h7-12H,1-6H2/t7-,8+,9+,10-,11-,12+^N
Key: KZNNISMAUNEBPT-KUDAMMAASA-N^N
InChI=1/C12H18/c1-7-2-11-3-8(1)10-4-9(7)5-12(11)6-10/h7-12H,1-6H2/t7-,8+,9+,10-,11-,12+
Key: KZNNISMAUNEBPT-KUDAMMAABM

Jmol-3D images

Image

SMILES

C1C2CC3CC1C4CC2CC3C4

Properties

Chemical formula

C₁₂H₁₈

Molar mass

163.56 g/mol

Structure

Point group

D_3h

Dipole moment

0 D

Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)

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Infobox references

Iceane is a saturated polycyclic hydrocarbon with formula C₁₂H₁₈. It has a cage-like molecular structure, whose carbon skeleton can be viewed as three fused cyclohexane rings in the "boat" conformation; or as two such rings in the "chair" conformation, connected by three parallel bonds.

The name "iceane" was proposed by the chemist Louis Fieser about a decade before the compound was first prepared. He was carrying out studies on the arrangement of water molecules in ice, when it occurred to him that there could exist a stable hydrocarbon with the above structure.

It is also referred to as wurtzitane,^[1] due to its similarity to the wurtzite crystal structure;^[2] however, the name "iceane" has precedence.

References

↑ Tobler, Hans; Klaus, Rolf Otto; Ganter, Camille (1975). "Wurtzitan (Tetracyclo\5.3.1.12,6.04,9]dodecan)". Helvetica Chimica Acta 58 (5): 1455. doi:10.1002/hlca.19750580522.
↑ Hamon, DPG; Taylor, GF (1976). "A synthesis of tetracyclo\5,3,1,12,6,04,9]dodecane (iceane)". Australian Journal of Chemistry 29 (8): 1721. doi:10.1071/CH9761721.

Iceane

See also

References

External links