Benzocyclooctatetraene

Benzocyclooctatetraene is a chemical compound with the formula C8H8. It is a derivative of cyclooctatetraene (COT), with a benzene ring fused to one edge. The molecule is not planar; the carbon atoms of the benzene ring and the two adjacent carbon atoms are coplanar, but the other six atoms of the COT ring are not. This compound is an important structure in the field of organic chemistry.

Structure and Bonding

Benzocyclooctatetraene is a non-planar molecule due to the steric strain between the hydrogen atoms. The molecule adopts a boat-like conformation, similar to cyclohexane. The carbon-carbon bonds in the benzene ring are of equal length, indicating the presence of resonance in the molecule.

Synthesis

Benzocyclooctatetraene can be synthesized from cyclooctatetraene via a Diels-Alder reaction with benzyne, followed by aromatization with palladium on carbon.

Reactions

Benzocyclooctatetraene undergoes reactions typical of an alkene, such as hydrogenation and halogenation. It also reacts with Lewis acids to form complexes.

Applications

While benzocyclooctatetraene itself has limited applications, its derivatives have been used in the synthesis of pharmaceuticals and dyes.

See also

• Cyclooctatetraene
• Benzene
• Diels-Alder reaction