Cathodic Reduction of Aliphatic Azides and of Azides, Activated by Olefinic and Carbonyl Groups

Article abstract of DOI:10.1007/BF00817905

In the majority of compounds investigated the main reduction path starting from azido compounds under parotic conditions leads to the retainment of one nitrogen in the product molecules, provided an initial phase of consumption of residual water is overcome.Good to excellent yields of N-acylated or nicely stable N,N-diacetylated aminoderivatives are obtainable.Even a secondary position of the original N3-group prevents diacetylation completely by steric reasons.Vicinal halogen cause the loss of all nitrogen atoms as does the presence of H⁺ in the case of azidocarbonyl compounds.Where reduction potential of the starting azide lies within the reduction range of Ac2O even high chemical yields of aminoderivatives are obtainable but with decrease of current efficiency.Reductive acetylation of benzoyl azide leads to the isolation of both rotational isomers of N-acetylbenzamide. - Keywords: Unsaturated Azides and Amines; α-Azido- and α-Aminocarbonylcompounds; Cathodic reduction