Cyclopentadienone is an
organic compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
with
molecular formula
A chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, such as paren ...
C
5H
4O. The parent cyclopentadienone is rarely encountered, because it rapidly
dimerize
In chemistry, dimerization is the process of joining two identical or similar Molecular entity, molecular entities by Chemical bond, bonds. The resulting bonds can be either strong or weak. Many symmetrical chemical species are described as dim ...
s. Many substituted derivatives are known, notably
tetraphenylcyclopentadienone
Tetraphenylcyclopentadienone is an organic compound with the formula . It is classified as a cyclic dienone. It is a dark purple to black crystalline solid that is soluble in organic solvents. It is an easily made building block for many organic a ...
. Such compounds are used as ligands in
organometallic chemistry
Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkali, alkaline earth, and transition metals, and so ...
.
left, The Knölker complex, derived from a substituted cyclopentadienone, is a catalyst for transfer hydrogenation.
Preparation
Cyclopentadienone can be generated by the photolysis or pyrolysis of various substances (e.g. 1,2-benzoquinone), and then isolated in an matrix isolation, argon matrix at . It dimerizes readily upon thawing the matrix at .
See also
*
Dienone
References
{{Cyclopentadienide complexes
Ketones
Fully conjugated nonaromatic rings