Manganese(III) acetate induced radical addition of azide to unsaturated fatty compounds

Nitrogen functionalities can be introduced in the alkyl chain of unsaturated fatty compounds by addition of azide mediated by manganese(III) acetate. The respective reaction of methyl oleate 1 containing an internal C,C double bond gave allyl azide 3 as a mixture of 4 regioisomers while the addition of azide to the terminal C,C double bond of methyl 10‐undecenoate 2 afforded the vicinal diazide 6 . Azide 3 could be easily converted to the saturated amine 4 by catalytic hydrogenation and to the allyl amines 5 by the Staudinger reaction.