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Tetraacetylethane

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Tetraacetylethane
Names
Other names 3,4-diacetyl-2,5-Hexanedione
Identifiers
CAS Number
PubChem CID
CompTox Dashboard (EPA)
Properties
Chemical formula C10H14O4
Molar mass 198.218 g·mol
Appearance white solid
Density 1.305 g/cm
Melting point 192–193 °C (378–379 °F; 465–466 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Tetraacetylethane is the organic compound with the nominal formula 2. It is a white solid that has attracted interest as a precursor to heterocycles and metal complexes. It is prepared by oxidation of sodium acetylacetonate:

I2 + 2 NaCH(C(O)CH3)2 → 2 + 2 NaI

Reminiscent of the case of acetylacetone, tetraacetylethane exists as the enol, as established by X-ray crystallography. The two C3O2H rings are twisted with a dihedral angle near 90°.

Many metal complexes have been prepared from the conjugate base of this ligand. One example is diruthenium(III) derivative 22, which is closely related to ruthenium(III) acetylacetonate.

References

  1. Robert G. Charles (1959). "Tetraacetylethane". Organic Syntheses. 39: 61. doi:10.15227/orgsyn.039.0061.
  2. Paula M. B. Piccoli, Thomas F. Koetzle, Arthur J. Schultz, Elizabeth A. Zhurova, Jernej Stare, A. Alan Pinkerton, Juergen Eckert, and Dusan Hadzi (2008). "Variable Temperature Neutron Diffraction and X-Ray Charge Density Studies of Tetraacetylethane". J. Phys. Chem. A. 112 (29): 6667–6677. Bibcode:2008JPCA..112.6667P. doi:10.1021/jp800204r. PMID 18593102.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. Koiwa, Tomohiro; Masuda, Yuki; Shono, Junpei; Kawamoto, Yuji; Hoshino, Yoshimasa; Hashimoto, Takeshi; Natarajan, Karuppannan; Shimizu, Kunio (2004). "Synthesis, Characterization, and Detailed Electrochemistry of Binuclear Ruthenium(III) Complexes Bridged by Bisacetylacetonate. Crystal and Molecular Structures of (Acac = 2,4-Pentanedionate Ion, tae = 1,1,2,2-Tetraacetylethanate Dianion)". Inorganic Chemistry. 43 (20): 6215–6223. doi:10.1021/ic030216c. PMID 15446866.
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