2,2,4,4-Tetramethylcyclobutanedione

Me4C4O2.png 144 2,2,4,4-Tetramethylcyclobutane-1,3-dione Tetramethyl-1,3-cyclobutanedione, Tetramethylcyclobuta-1,3-dione 933-52-8 13617 213-269-6 RT4AQ22KS4 13028 3183999 1S/C8H12O2/c1-7(2)5(9)8(3,4)6(7)10/h1-4H3 RGCDVHNITQEYPO-UHFFFAOYSA-N CC1(C(=O)C(C1=O)(C)C)C 8 12 2 Colorless or white solid 112-115 2,2,4,4-Tetramethylcyclobutanedione is the organic compound with the formula (CH3)4C4O2. The compound is a diketone of cyclobutane, bearing four methyl groups. It is a white solid that is used as a precursor to diverse industrial products. Synthesis and reactions 2,2,4,4-Tetramethylcyclobutanedione is the head-to-tail dimer of dimethylketene. It arises spontaneously when dimethylketene is produced by dehydrohalogenation of isobutyryl chloride with triethylamine.R. Huisgen, P. Otto J. Am. Chem. Soc. The mechanism of dimerization of dimethylketene 90 19 5342–5343 1968 10.1021/ja01021a090 In the presence of aluminium trichloride, 2,2,4,4-tetramethylcyclobutanedione isomerizes to the lactone dimethylketene dimer (4-isopropylidene-3,3-dimethyl-2-oxetanone).Organic Syntheses R.H. Hasek R.D. Clark G.L. Mayberry Dimethylketene β-Lactone Dimer 1968 48 72 10.15227/orgsyn.048.0072 free Dimethylketene dimer is a precursor to various alkyl ketene dimers, which are used in papermaking. 350px|center|Isomerisierung von Tetramethyl-1,3-cyclobutandion zum Dimethylketendimer Isomerisation of tetramethyl-1,3-cyclobutanedione to Dimethyl ketene dimer Hydrogenation of 2,2,4,4-tetramethylcyclobutanedione gives 2,2,4,4-tetramethylcyclobutanediol, which is of interest in polymer chemistry. References Category:Diketones Category:Cyclic ketones