Tetraphenylcyclopentadienone

Tetraphenylcyclopentadienone is a chemical compound with the formula (C6H5)4C5O. It is a yellow solid that is soluble in common organic solvents. This compound is used in the preparation of other organic compounds.

Structure and synthesis

Tetraphenylcyclopentadienone is a cyclopentadienone with four phenyl groups attached to the carbon atoms of the five-membered ring. The molecule is planar, which is consistent with the fact that it is highly conjugated. The compound is synthesized by the condensation of benzil and dibenzyl ketone in the presence of base.

Reactions

Tetraphenylcyclopentadienone undergoes several reactions that are characteristic of carbonyl compounds. For example, it forms a hydrazone upon treatment with phenylhydrazine. It also undergoes the Aldol reaction with ketones to give alcohols.

Applications

Tetraphenylcyclopentadienone is used in the synthesis of other organic compounds. For example, it is a precursor to bisdiphenylene-phenylphosphine oxide, a ligand used in organometallic chemistry. It is also used in the preparation of cyclopentadienyl complexes of transition metals.

Safety

Like many organic compounds, tetraphenylcyclopentadienone should be handled with care. It can cause irritation to the skin and eyes, and may be harmful if swallowed or inhaled.

References

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