Chemistry of Heterocyclic Compounds

, Volume 13, Issue 10, pp 1083–1086 | Cite as

Acetals of lactams and acid amides

XXI. Polarographic study of enamino ketones of the pyrrolidine, piperidine, and hexahydroazepine series
  • V. G. Granik
  • A. B. Grigor'ev
  • M. K. Polievktov


The reduction of 1-methyl-2-(2-benzoyl)methylenepyrrolidine, hexahydroazepines IIa–c, and (β-dimethylamino-β-methyl)methyleneacetophenone III in aprotic media on a dropping mercury electrode proceeds in two one-electron steps to give the corresponding enamines with a benzhydryl residue in the 2′ position. The regular dependence of the E1/2 values of the first waves in the reduction of enamino ketones IIa–c on the ring size is discussed: six-membered enamino ketone IIb is reduced most easily, while five-membered IIa is reduced with the greatest difficulty. It is shown that the ring size of the enamino compounds affects the E1/2 values only in those cases in which a change in the hybridization of the ring carbon atom occurs during electrical reduction.


Mercury Amide Carbon Atom Ketone Great Difficulty 
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Copyright information

© Plenum Publishing Corporation 1978

Authors and Affiliations

  • V. G. Granik
    • 1
  • A. B. Grigor'ev
    • 1
  • M. K. Polievktov
    • 1
  1. 1.S. Ordzhonikidze All-Union Scientific-Research Pharmaceutical-Chemistry InstituteMoscow

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