NEW RESULTS ON FREE-RADICAL ADDITIONS TO UNSATURATED FATTY COMPOUNDS

Unsaturated fatty acids such as oleic acid are 1,2-dialkyl substituted alkenes, which can be functionalized by free radical addition to the C,C-double bond. We have been able to add enolizable compounds, e.g. acetone, acetic acid and malonic acid to methyl oleate mediated by manganese(III)acetate. Azide radicals, generated by manganese(III)acetate-oxidation of sodium azide, have also been added to methyl oleate. Perfluoroalkyl iodides have been added via perfluoroalkyl radicals to methyl 10-undecenoate and methyl oleate to form the corresponding addition products. Reduction of the iodides by tributyltin hydride and saponification leads to interesting partially fluorinated fatty acids.