2,2,4,4-Tetramethylcyclobutanedione

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.

It arises spontaneously when dimethylketene is produced by dehydrohalogenation of isobutyryl chloride with triethylamine.

[1] In the presence of aluminium trichloride, 2,2,4,4-tetramethylcyclobutanedione isomerizes to the lactone dimethylketene dimer (4-isopropylidene-3,3-dimethyl-2-oxetanone).

Hydrogenation of 2,2,4,4-tetramethylcyclobutanedione gives 2,2,4,4-tetramethylcyclobutanediol, which is of interest in polymer chemistry.

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