Tetraacetylethane

Tetraacetylethane is the organic compound with the nominal formula [CH(C(O)CH3)2]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:[1]

I2 + 2 NaCH(C(O)CH3)2 → [CH(C(O)CH3)2]2 + 2 NaI
Tetraacetylethane
Names
Other names
3,4-diacetyl-2,5-Hexanedione
Identifiers
Properties
C10H14O4
Molar mass 198.218 g·mol−1
Appearance white solid
Density 1.305 g/cm3
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 [77 °F], 100 kPa).
Infobox references

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°.[2]

Many metal complexes have been prepared from the conjugate base of this ligand. One example is diruthenium(III) derivative [Ru(acac)2]2[C(C(O)CH3)2]2, which is closely related to ruthenium(III) acetylacetonate.[3]

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 [{Ru(acac)2}2(tae)] (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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