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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
Article
  • 28 Downloads

Abstract

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.

Keywords

Mercury Amide Carbon Atom Ketone Great Difficulty 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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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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