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Russian Journal of Organic Chemistry

, Volume 41, Issue 1, pp 134–140 | Cite as

Alkylation of 3,4-Dibromo-4-methyltetrahydropyran with Diethyl Malonate as a Key to Understanding the Electronic Nature of Chemo- and Regioselectivity of Molecules

  • A. A. Gevorkyan
  • A. S. Arakelyan
  • Zh. L. Dzhandzhulyan
  • A. R. Mikaelyan
  • K.A. Petrosyan
  • G. A. Panosyan
Article

Abstract

The reaction of 3,4-dibromo-4-methyltetrahydropyran with diethyl malonate in the presence of sodium butoxide leads to formation of the corresponding cross-coupling product rather than of tetraethyl ethane-1,1,2,2-tetracarboxylate (product of dehydrodimerization of diethyl malonate) which is formed in the presence of sodium ethoxide. An explanation was proposed, which may be regarded as a key to understanding the nature of the driving force for one- and two-electron transfer, as well as chemo- and regioselectivity of organic molecules.

Keywords

Sodium Organic Chemistry Diethyl Alkylation Organic Molecule 
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

© MAIK “Nauka/Interperiodica” 2005

Authors and Affiliations

  • A. A. Gevorkyan
    • 1
  • A. S. Arakelyan
    • 1
  • Zh. L. Dzhandzhulyan
    • 1
  • A. R. Mikaelyan
    • 1
  • K.A. Petrosyan
    • 1
  • G. A. Panosyan
    • 2
  1. 1.Institute of Organic ChemistryNational Academy of Sciences of ArmeniaErevanArmenia
  2. 2.Molecular Structure Research CenterNational Academy of Sciences of ArmeniaArmenia

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