Iceane

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Iceane
IUPAC name	Tetracyclo[5.3.1.12,604,9]dodecane
Other names	Iceane
Identifiers
CAS number	[53283-19-5]
SMILES	C1C2CC3CC1C1CC2CC3C1
InChI	1/C12H18/c1-7-2-11-3-8(1)10-4-9(7)5- 12(11)6-10/h7-12H,1-6H2
Properties
Molecular formula	C12H18
Molar mass	163.56 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Iceane (C₁₂H₁₈) is a saturated hydrocarbon variant of adamantane. The structure of iceane resembles a cage formed by three fused boat cyclohexanes - or alternately two chair cyclohexanes connected by three axial bonds. Its name 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 the three vertical hexagons with boat conformations, linked by three equatorial hydrogen bonds, could indicate the existence of a stable hydrocarbon counterpart. This gave rise to the name iceane which refers to the fact that it resembles the shape of ice.

[edit] External links

• Royal Society of Chemistry Journal
• Symmetry Through the Eyes of a Chemist, Magdolna Hargittai
• A Basis for Synthesis Design, Tse-Lok Ho
• Structures and Energies of Polycyclic Hydrocarbons, Joan E. Shields