Tetraphenylcyclopentadienone

It is a dark purple to black crystalline solid that is soluble in organic solvents.

The C5O core of the molecule is planar and conjugated, but the bonds have a definite alternating single- and double-bond nature.

[3] Unlike the parent compound cyclopentadienone, which rapidly dimerizes,[4] the tetraphenyl derivative is isolable at room temperature.

Tetraphenylcyclopentadienone can be synthesized by a double aldol condensation involving benzil and dibenzyl ketone in the presence of a basic catalyst.

[7] Tetraphenylcyclopentadienone can provide an effective alternative to DDQ in aromatization of porphyrins:[8] Tetraarylcyclopentadienones are a well studied class of ligands in organometallic chemistry.

Skeletal formula
The Shvo catalyst is a ruthenium complex of tetraphenylcyclopentadienone