Tetraacetylethane Explained
Tetraacetylethane is the organic compound with the nominal formula [CH(C(O)CH<sub>3</sub>)<sub>2</sub>]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)CH<sub>3</sub>)<sub>2</sub>]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°.[2]
Many metal complexes have been prepared from the conjugate base of this ligand. One example is diruthenium(III) derivative [Ru(acac)<sub>2</sub>]2[C(C(O)CH<sub>3</sub>)<sub>2</sub>]2, which is closely related to ruthenium(III) acetylacetonate.[3]
References
- 10.15227/orgsyn.039.0061. Tetraacetylethane. Organic Syntheses. 1959. 39. 61. Robert G. Charles.
- 10.1021/jp800204r. Variable Temperature Neutron Diffraction and X-Ray Charge Density Studies of Tetraacetylethane. Paula M. B. Piccoli, Thomas F. Koetzle, Arthur J. Schultz, Elizabeth A. Zhurova, Jernej Stare, A. Alan Pinkerton, Juergen Eckert, and Dusan Hadzi. J. Phys. Chem. A. 2008. 112. 29 . 6667–6677. 18593102 . 2008JPCA..112.6667P .
- 10.1021/ic030216c. Synthesis, Characterization, and Detailed Electrochemistry of Binuclear Ruthenium(III) Complexes Bridged by Bisacetylacetonate. Crystal and Molecular Structures of [{Ru(acac)<sub>2</sub>}2(tae)] (Acac = 2,4-Pentanedionate Ion, tae = 1,1,2,2-Tetraacetylethanate Dianion). 2004. Koiwa. Tomohiro. Masuda. Yuki. Shono. Junpei. Kawamoto. Yuji. Hoshino. Yoshimasa. Hashimoto. Takeshi. Natarajan. Karuppannan. Shimizu. Kunio. Inorganic Chemistry. 43. 20. 6215–6223. 15446866.
