Cathodic Reductions of Acid Azides. Electrolytic Studies on Vinyl Acides, VIII

Article abstract of DOI:10.1007/BF00810418

The cathodic reduction of the O=C-N3-system in aprotic solvent in the presence of anhydrides proves to be a convenient way to triacylammonia derivatives.Using the complexation of Li(+) ions with the acid azide this synthetic methods can start from non-dangerous acid halides.The complex formation constant has been estimated and the chemical stability of N,N-diacylamides produced has been investigated.Mechanistic details about the role of Li(+)-ions in these electrolyses are given.Further reduction of the triacylammonia derivatives at more negative potentials results in protected aldehydic functions, i.e. 1-acyloxy-1-diacylaminomethanes, in good yields. - Keywords: Acid azides; N,N-Diacylamides; 1-Acyloxy-1-diacetyl-aminomethanes; Lithiumion-azide complexes; Cathodic reduction