The electrolyses of tert.-butyl and tert.-amyl amines were run with a voltage of approximately 3v., as measured across the cell, with and without the presence of 1-2% nitro-tert.-alkane. A graphite anode was used; the supporting electrolyte was NaClO4; the solvent was the reacting amine(s) with 10-20% water to solubilize the NaClO4. The products were azo compounds, azoxy compounds, 1,3-disubstituted ureas and traces of nitroso compounds. In the case of tert.-butyl amine di-tert.-butyl carbodiimide was also shown to be a product. The presence of nitro compounds increased the yields of azoxy and nitroso compounds and decreased the yields of azo compounds. The nitro compounds were consumed during the electrolyses and the fate of the alkyl groups was to become bonded to the nitrogen atom bonded to oxygen in an azoxy product. These results were interpreted in terms of a nitrene intermediate.
College and Department
Chemistry and Biochemistry
BYU ScholarsArchive Citation
Bergen, Karl Lloyd, "The effect of nitroalkanes on the electrolytic oxidation of tertiary butyl amine and tertiary amyl amine" (1975). Theses and Dissertations. 8167.
Amines, Electrolytic oxidation