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Cyclopentanone is common precursor to fragrances, especially those related to jasmine and jasmone. Examples include 2-pentyl- and 2-heptylcyclopentanone. [4] It is a versatile synthetic intermediate, being a precursor to cyclopentobarbital. [5] Cyclopentobarbital, a drug made from cyclopentanone
2-Cyclopentenones can be synthesized in a number of ways. One of the routes involves elimination of α-bromo-cyclopentanone using lithium carbonate [2] and Claisen condensation-decarboxylation-isomerization cascades of unsaturated diesters as shown below. [3] Industrial synthesis of cyclopentenone
The synthesis of the compound is carried out by a radical addition of cyclopentanone to (+)-limonene under oxygen in acetic acid. As a catalyst, manganese(II) acetate and cobalt(II) acetate are used. [2]
For instance, the reaction of cyclopentanone with diazomethane forms cyclohexanone (shown below). The Büchner ring expansion reactions utilizing diazoalkanes have proven to be synthetically useful as they can not only be used to form 5- and 6-membered rings, but also more unstable 7- and 8-membered rings. [27]
Dimethyl malonate is used extensively in the fragrance industry as a raw material in the synthesis of jasmonates. For example, methyl dihydrojasmonate is synthesized from cyclopentanone , pentanal and dimethyl malonate. [ 3 ]
A more approachable laboratory synthesis of disubstituted cubane involves bromination of the ethylene ketal of cyclopentanone to give a tribromocyclopentanone derivative. Subsequent steps involve dehydrobromination, Diels-Alder dimerization, etc. [9] [10] Alternative synthesis of a disubstituted cubane
Initial synthesis gave a racemic form of the compound using an intramolecular etherification reaction of the alcohol motifs and the double bond. Yamamoto and coworkers report the use of an alternative intramolecular Robinson annulation to provide a straightforward enantioselective synthesis of tetracyclic core of platensimycin.
The Baeyer–Villiger oxidation is an organic reaction that forms an ester from a ketone or a lactone from a cyclic ketone, using peroxyacids or peroxides as the oxidant. [1] The reaction is named after Adolf von Baeyer and Victor Villiger who first reported the reaction in 1899.