Tetraphenylcyclopentadienone

Chembox new
Name = Tetraphenylcyclopentadienone
ImageFile = Tetraphenylcyclopentadienone.png ImageSize = 200px
IUPACName = 2,3,4,5-Tetraphenyl-2,4- cyclopentadien-1-one
OtherNames = Tetracyclone, TPCP
Section1 = Chembox Identifiers
CASOther = [479-33-4] [ [http://chemfinder.cambridgesoft.com ChemBioFinder ] ]
SMILES = O=C2C(=C(C(=C2c1ccccc1) c3ccccc)c4ccccc4)c5ccccc5
Section2 = Chembox Properties
Formula = C₂₉H₂₀O
MolarMass = 384g/mol [ [http://msds.chem.ox.ac.uk/TE/tetraphenylcyclopentadienone.html MSDS Physical Chemistry Laboratory, Oxford University ] ]
MeltingPt = 218-220 °C

Tetraphenylcyclopentadienone is a dark purple to black crystalline solid at standard temperature and pressure. Because of its highly conjugated nature, it can be analyzed in the UV spectrum.

Tetraphenylcyclopentadienone is a "propeller" shape in 3D because of sterics.

ynthesis

Tetraphenylcyclopentadienone is used as the diene in the Diels-Alder synthesis of 1,2,3,4-tetraphenylnaphthalene, commonly carried out in the undergraduate organic teaching laboratory, with benzyne as the dienophile.

It can also be made using the Aldol condensation with benzil and dibenzyl ketone (1,3-diphenyl-2-propanone). This reaction is also a common experiment in the undergraduate organic chemistry labs.

References