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Keywords:

  • Azide;
  • Amine;
  • Manganese(III) acetate;
  • Methyl oleate;
  • Renewable

Abstract

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.