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Ketonization of Carboxylic Acids by Decarboxylation: Mechanism and Scope
Author(s) -
Renz Michael
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400546
Subject(s) - decarboxylation , chemistry , cyclopentanone , ketone , acetone , mechanism (biology) , organic chemistry , reaction mechanism , carboxylic acid , catalysis , philosophy , epistemology
In the ketonic decarboxylation process, a ketone is formed from two moles of carboxylic acid; water and carbon dioxide are produced as side‐products. At present, the mechanism of this reaction remains under debate; it has been proposed as a radical mechanism, a mechanism involving a ‐keto acid as intermediate, or a concerted mechanism. This paper demonstrates that the latter mechanism is the most likely one and that weak bases may play the role of promoters. Different processes are reviewed for the syntheses of the following ketones: symmetrical ketones, such as acetone or 3‐pentanone, cyclic ketones, such as cyclopentanone (parent compound and substituted derivatives), fatty ketones, and some unsymmetrical ketones. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)