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2,2,4,4-Tetramethylcyclobutanedione

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2,2,4,4-Tetramethylcyclobutanedione
Names
Preferred IUPAC name 2,2,4,4-Tetramethylcyclobutane-1,3-dione
Other names Tetramethyl-1,3-cyclobutanedione, Tetramethylcyclobuta-1,3-dione
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.012.063 Edit this at Wikidata
EC Number
  • 213-269-6
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H12O2/c1-7(2)5(9)8(3,4)6(7)10/h1-4H3Key: RGCDVHNITQEYPO-UHFFFAOYSA-N
SMILES
  • CC1(C(=O)C(C1=O)(C)C)C
Properties
Chemical formula C8H12O2
Molar mass 140.182 g·mol
Appearance Colorless or white solid
Melting point 112–115 °C (234–239 °F; 385–388 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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.

In the presence of aluminium trichloride, 2,2,4,4-tetramethylcyclobutanedione isomerizes to the lactone dimethylketene dimer (4-isopropylidene-3,3-dimethyl-2-oxetanone). Dimethylketene dimer is a precursor to various alkyl ketene dimers, which are used in papermaking.

Isomerisierung von Tetramethyl-1,3-cyclobutandion zum Dimethylketendimer Isomerisation of tetramethyl-1,3-cyclobutanedione to Dimethyl ketene dimer
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

  1. R. Huisgen, P. Otto (1968), "The mechanism of dimerization of dimethylketene", J. Am. Chem. Soc., vol. 90, no. 19, pp. 5342–5343, doi:10.1021/ja01021a090
  2. R.H. Hasek; R.D. Clark; G.L. Mayberry (1968). "Dimethylketene β-Lactone Dimer". Organic Syntheses. 48: 72. doi:10.15227/orgsyn.048.0072.
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