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:
mrenz
itq.upv.es
M. Renz, A. Corma, Eur. J. Org. Chem., 2004, 2036-2039.
DOI: 10.1002/ejoc.200300778
Abstract
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.
see article for more examples
proposed mechanism
Key Words
Base Catalysis, Carboxylic Acids, Cyclopentanones, Ketonic Decarboxylation
ID: J24-Y2004-360
