cyclobutanone

Cyclobutanone is a four-membered cyclic ketone with the formula C4H6O. Its carbonyl group is part of a highly strained cyclobutane ring, which influences its chemistry and makes certain reactions more favorable than with larger rings. At room temperature it is a colorless liquid that is miscible with many organic solvents and only sparingly soluble in water. Synthesis commonly involves oxidation of cyclobutanol derivatives, and industrial routes exist that construct the four-carbon ring prior to introducing the carbonyl. In laboratory settings, oxidation of cyclobutanol with reagents such as PCC or Jones-type oxidants is typical. Reactions of cyclobutanone are accelerated by ring strain: Baeyer-Villiger oxidation converts cyclobutanone to gamma-butyrolactone, a valued synthetic intermediate; nucleophilic additions to the carbonyl can lead to ring-opening products, and various rearrangements are used to access more complex structures. Applications include use as a versatile building block in organic synthesis, enabling access to lactones, lactams and other ring-constrained frameworks important in medicinal chemistry. Safety considerations note that cyclobutanone is flammable and can irritate skin and eyes; it should be handled in a well-ventilated area with appropriate protective equipment.