1,5-cyclooctadiene

1,5-Cyclooctadiene is an organic compound with the formula (CH₂)₆(CH=CH)₂. It is a colorless liquid with a strong, sweet odor. This cyclic compound is an important intermediate in the production of various chemicals and polymers.

Structure and Properties

1,5-Cyclooctadiene is a cyclic hydrocarbon with two double bonds. The molecule is not planar; instead, it adopts a "puckered" conformation known as a "boat conformation". This conformation reduces the amount of steric hindrance between the hydrogen atoms on the adjacent carbon atoms.

The double bonds in 1,5-cyclooctadiene are not conjugated, meaning they do not share a continuous overlap of p-orbitals. As a result, the compound does not exhibit the coloration or stability often associated with conjugated double bonds.

Synthesis

1,5-Cyclooctadiene can be synthesized from 1,3-butadiene through a process known as dimerization. This reaction is typically catalyzed by transition metal complexes, such as those of nickel or palladium.

Applications

1,5-Cyclooctadiene is primarily used as a building block in the synthesis of other chemicals. It can be hydrogenated to produce cyclooctane, or it can be oxidized to produce cyclooctene. It is also used in the production of polymers and resins.

Safety

Like many organic solvents, 1,5-cyclooctadiene is flammable and should be handled with care. It can cause irritation to the skin and eyes, and prolonged exposure can lead to respiratory problems.

See Also

• Cyclooctene
• Cyclooctane
• 1,3-Butadiene