Perspective view, showing the canted phenyl rings
Tetracyclone, TPCPD, Cyclone
3D model (JSmol)
|Molar mass||384.48 g·mol−1|
|Melting point||219 to 220 °C (426 to 428 °F; 492 to 493 K)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Tetraphenylcyclopentadienone is an organic compound with the formula (C6H5)4C4CO. 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 and organometallic compounds.
The C5O core of the molecule is planar and conjugated. The C2-C3 and C4-C5 distances are 1.35 Å, while the C1-C2, C3-C4, C5-C1 are closer to single bonds with distances near 1.5 Å. The phenyl groups of tetraphenylcyclopentadienone adopt a "propeller" shape in its 3D conformation. The four phenyl rings are rotated out of the plane of the central ring because of steric repulsion with each other.
The central ring can act as a diene in Diels–Alder reactions with various dienophiles. For example, reaction with benzyne leads to 1,2,3,4-tetraphenylnaphthalene and reaction with diphenylacetylene leads to hexaphenylbenzene. In this way, it is a precursor to graphene-like molecules, such as coronene.
Ligand in organometallic chemistry
- J. C. Barnes; W. M. Horspool; F. I. Mackie (1991). "2,3,4,5-Tetraphenylcyclopenta-2,4-dien-1-one and 5,6,7,8-tetrachloro-3a,9a-dihydro-2,3,3a,9a-tetraphenylcyclopenta[2,3-b][1,4]benzodioxin-1-one–toluene (2/1): Compounds of photochemical interest". Acta Crystallogr. C. 47: 164–168. doi:10.1107/S0108270190005145.
- John R. Johnson, J. R.; Grummitt, O. (1943). "Tetraphenylcyclopentadienone". Organic Syntheses. 23: 92. ; Collective Volume, 3, p. 805
- Sheley, C. F.; Shechter, H. (1970). "Cyclopentadienones from 1,2,4-cyclopentanetriones, 2-cyclopentene-1,4-diones, and 3-cyclopentene-1,2-diones". The Journal of Organic Chemistry. 35 (7): 2367–2374. doi:10.1021/jo00832a058.
- Fieser, L. F. (1966). "Hexaphenylbenzene". Organic Syntheses. 46: 44.; Collective Volume, 5, p. 604
- Feng, Xinliang; Pisula, Wojciech; Müllen, Klaus (31 January 2009). "Large polycyclic aromatic hydrocarbons: Synthesis and discotic organization". Pure and Applied Chemistry. 81 (12). doi:10.1351/PAC-CON-09-07-07.
- M.A. Filatov; A.Y. Lebedev; S.A. Vinogradov; A.V. Cheprakov (2008). "Synthesis of 5,15-Diaryltetrabenzoporphyrins". J. Org. Chem. 73 (11): 4175–4185. doi:10.1021/jo800509k. PMC 2491715.
- Quintard, Adrien; Rodriguez, Jean (14 April 2014). "Iron Cyclopentadienone Complexes: Discovery, Properties, and Catalytic Reactivity". Angewandte Chemie International Edition. 53 (16): 4044–4055. doi:10.1002/anie.201310788. PMID 24644277.