Catalytic C,C-bond forming additions to unsaturated fatty compounds
- Author(s): Ursula Biermann, Juergen O. Metzger
- Title: Catalytic C,C-bond forming additions to unsaturated
- Date of Upload: 2004
- Article: Topics in Catalysis Vol. 27, Nos. 1–4, February 2004, University
of Oldenburg, Department of Chemistry, D-26111 Oldenburg, Germany
- Keywords: renewable raw materials, unsaturated fatty acids, C,C-bond
forming reactions, catalysts, Lewis acids, substainable development, vegetable
oil, plant oil
- Abstract:
- A large number of novel fatty compounds have been synthesized by catalytic
C,C-bond forming addition reactions to the C,Cdouble bond of unsaturated fatty
compounds. Radical reactions such as the solvent-free addition of a-halocarboxylic
acid esters initiated by electron transfer, e.g., from copper to give fat-derived
g-lactones are described as well as Lewis
acid–induced electrophilic addition reactions yielding new oleochemicals such
as alkyl-substituted 4-chlorotetrahydropyrans,
primary homoallylic alcohols, b-, g-unsaturated
ketocarboxylic acids and Diels–Alder addition products. New catalysts as,
e.g., ligandmodified rhodium catalysts for the hydroformylation and heterogeneous
boron-modified rhenium catalysts for the olefin metathesis have been developed.
The addition of C-nucleophiles such as dimethylmalonate and nitromethane is
possible by palladium-(0)catalyzed additions to unsaturated fatty compounds
after conversion of the electron-rich to an electron-poor double bond. More
than fifty literature articles are reviewed.
- URL: http://www.chemie.uni-oldenburg.de/oc/metzger/publikationen/pdf/102.pdf
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