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Influence of the nature of the base electrolyte on the regioselectivity of the cathodic hydrodimerization of 1-acetylnaphthalene in an aprotic medium

  • V. P. Gul'tyai
  • T. Ya. Rubinskaya
  • A. S. Mendkovich
Organic Chemistry
  • 18 Downloads

Abstract

The electrolysis of 1-acetylnaphthalene at a controlled potential [DMF, Ba· (CIO4)2] leads to the formation of 5-acetyl-1,2,4,5-tetrahydro-2-methyl-2-(1-naphthyl)-1, 4-methano-3-benzoxepine (yield of 60%); this is explained by the stabilization of the dimeric dianion of the “head-tail” type by the Ba2+ cations. The formation of 2,3-dimethyl-2,3-di-(1-naphthyl)-butane-2,3-diol is observed with the acylotropic rearrangement of the intermediate anion, leading to 2-acetylnaphthalene, in the presence of lithium cations.

Keywords

Lithium Diol Control Potential Base Electrolyte Lithium Cation 
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Copyright information

© Plenum Publishing Corporation 1991

Authors and Affiliations

  • V. P. Gul'tyai
    • 1
  • T. Ya. Rubinskaya
    • 1
  • A. S. Mendkovich
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow

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