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Ketonic Decarboxylation Catalysed by Weak Bases and Its Application to an Optically Pure Substrate

Michael Renz*, Avelino Corma

*Instituto de Tecnología Química, UPV-CSIC, Universidad Politécnica de Valencia Avda. de los Naranjos s/n, 46022 Valencia, Spain, Email:

M. Renz, A. Corma, Eur. J. Org. Chem., 2004, 2036-2039.

DOI: 10.1002/ejoc.200300778


Catalytic amounts of weak bases such as sodium carbonate can carry out the ketonic decarboxylation of adipic acid into cyclopentanone selectively. This is in accordance with a mechanism involving decarboxylation and nucleophilic attack at a second carboxyl group. Stereogenic centres in the β-positions retain their stereochemistry.

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proposed mechanism

Key Words

Base Catalysis, Carboxylic Acids, Cyclopentanones, Ketonic Decarboxylation

ID: J24-Y2004-360