ELECTROCHEMICAL IODINATION OF TRIACETONEAMINE - SYNTHESIS OF 3-CARBAMOYL-2,2,5,5-TETRAMETHYLPYRROLYDINE

Reaction of electrochemical iodination of 2,2,6,6-tetramethyl-4-piperi done (triacetoneamine, TAA) in electrolyte TAA-KI-KOH-NH3 was studied, It was shown that TAA iododerivatives undergo in statu nascendi the F avorskii rearrangement with formation of corresponding amides of the a cids. 3-Carbamoyl-2,2,5,5-tetramethylpyrrolidine is the main product o f this reaction, The product of KIO3 reduction can be an iodinating ag ent in this reaction, However, in this case the reaction is accompanie d by significant TAA tarring, On the basis of the results obtained, a preparative procedure for synthesizing 3-carbamoyl-2,2,5,5-tetramethyl pyrrolidine, which is an important starting compound for the spin labe l synthesis, was developed.