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Cyclopentanone

Cyclopentanone is the organic compound with the formula (CH<sub>2</sub>)<sub>4</sub>CO. This cyclic ketone is a colorless volatile liquid.

Preparation

Ketonic decarboxylation of adipic acid gives cyclopentanone. The reaction is conducted at elevated temperatures in the presence of barium hydroxide.

The Pd-catalyzed oxidation of cyclopentene also gives cyclopentanone.

Uses

Cyclopentanone is common precursor to fragrances, especially those related to jasmine and jasmone. Examples include 2-pentyl- and 2-heptylcyclopentanone. It is a versatile synthetic intermediate, being a precursor to cyclopentobarbital.

Cyclopentanone is also used to make cyclopentamine, the pesticide pencycuron, and pentethylcyclanone.

It is also used as a precursor to cubane-1,4-dicarboxylate, which is used to synthesize other substituted cubanes, such as the high explosives heptanitrocubane and octanitrocubane.

References