Twistane

 ( Polycyclic Nonaromatic Hydrocarbons ) 

Twistane (IUPAC name: tricyclo4.4.0.0^3,8decane) is an organic compound with the chemical formula Carbon₁₀Hydrogen₁₆. It is a cycloalkane and an isomer of the simplest diamondoid, adamantane, and like adamantane, is not very volatile. Twistane was named for the way its rings are permanently forced into the cyclohexane conformation known as the "twist-boat". The compound was first reported by Whitlock in 1962.

---

Synthesis Twistane has been synthesized in a variety of ways. The original 1962 method was based on a bicyclo2.2.2octane framework. A 1967 publication concerned an intramolecular aldol condensation of a cis-decalin diketone. It is formed when basketane is hydrogenated.

---

Symmetry

The only symmetry operation in twistane is rotation, and there exist three 2-fold axes as shown in the left picture. Thus the point group of twistane is D₂. Although twistane has four , it only exists as two . This is because it is symmetric along its C₂ axis.

---

Polytwistane

Polytwistane is a hypothetical polymer of fused twistane units awaiting actual synthesis.

Categories: Polycyclic Nonaromatic Hydrocarbons, Tricyclic Compounds

Post Comment