Cyclobutanone

DescriptionCyclobutanone is an organic compound with a four-membered cyclic ketone. It is used in preparation of cyclobutane derivatives, as a starting material for aminocyclobutanecarboxylic acid through sulfonyloxiranes, to prepare dihydro-furan-2-one in presence of polystyrene-bound phenylselenic acid as catalyst. It is also involved in the photochemical synthesis of nucleoside analogues such as bicyclic nucleosides and isonucleosides. Furthermore, it is used to synthesis fatty acid, 2-oxo-cyclobutane undecanoic acid, which is used in the development of an enzyme-linked immunosorbent assy for the detection of irradiated foods.

UsesCyclobutanone is used in preparation of cyclobutane derivatives. It is used as a starting material for aminocyclobutanecarboxylic acid through sulfonyloxiranes. It is also used to prepare dihydro-furan-2-one in presence of polystyrene-bound phenylselenic acid as catalyst. Further, it is involved in the photochemical synthesis of nucleoside analogues such as bicyclic nucleosides and isonucleosides.

PreparationThe Russian chemist Nikolai Kischner first prepared cyclobutanone in 1905. He synthesized cyclobutanone in a low yield from cyclobutanecarboxylic acid in several reaction steps.Another synthesis of cyclobutanone involves lithium-catalyzed rearrangement of oxaspiropentane, which is formed by epoxidation of the easily accessible methylenecyclopropane.