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 (application/pdf)


This shadow-file was created by My Meta Maker 1.6.1. Last Update: Thu Jun 3 11:35:05 2004