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


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.


Sodium Organic Chemistry Diethyl Alkylation Organic Molecule 
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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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