1,5-Cyclooctadiene

1,5-Cyclooctadiene (also known as COD or 1,5-COD) is a organic chemical compound with the chemical formula C₈H₁₂. It is a colorless liquid with a strong, sweet odor and is used in various chemical syntheses.

Structure and Properties

1,5-Cyclooctadiene is a cyclic compound with eight carbon atoms and two double bonds. The molecule adopts a "crown" conformation, where the plane of the molecule is not flat but puckered. This conformation is due to the steric repulsion between the hydrogen atoms on the carbon atoms.

The compound is a dienophile and can undergo Diels-Alder reactions with various dienes. It is also a ligand in organometallic chemistry, where it can bind to transition metals to form complexes.

Synthesis

1,5-Cyclooctadiene can be synthesized from 1,3-butadiene through a dimerization reaction. This reaction is typically catalyzed by nickel or palladium complexes.

Applications

1,5-Cyclooctadiene is used in the synthesis of various organic compounds, including pharmaceuticals and polymers. It is also used as a ligand in organometallic chemistry, where it can form complexes with transition metals.

Safety

1,5-Cyclooctadiene is flammable and should be handled with care. It can cause skin and eye irritation, and prolonged exposure can lead to respiratory problems.

See Also

• Cyclooctene
• Cyclooctane
• Organic chemistry
• Organometallic chemistry