Iceane

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

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