Electrochemical Iodination of Triacetoneamine: Synthesis of 3-Carbamoyl-2,2,5,5-Tetramethylpyrrolydine

E. Sh. Kagan , I. Yu. Zhukova , S. A. Pozhidaeva , E. I. Kovalenko
Российский электрохимический журнал
Abstract / Full Text

Reaction of electrochemical iodination of 2,2,6,6-tetramethyl-4-piperidone (triacetoneamine,TAA) in electrolyte TAA–KI–KOH–NH3 was studied. It was shown that TAA iododerivatives undergo in statunascendi the Favorskii rearrangement with formation of corresponding amides of the acids. 3-Carbamoyl-2,2,5,5-tetramethylpyrrolidine is the main product of this reaction. The product of KIO3 reduction can be aniodinating agent in this reaction. However, in this case the reaction is accompanied by significant TAA tarring.On the basis of the results obtained, a preparative procedure for synthesizing 3-carbamoyl-2,2,5,5-tetrameth-ylpyrrolidine, which is an important starting compound for the spin label synthesis, was developed.