Russian Journal of Organic Chemistry

, Volume 45, Issue 1, pp 26–29 | Cite as

Metalation of toluene and cumene with alkali metal-crown ether complexes

  • A. L. Shabanov
  • N. M. Seidov
  • U. A. Gasanova
  • Z. O. Kakhramanova
  • M. M. Gasanova


Metalation of toluene and isopropylbenzene with alkali metal-crown ether complexes led to the corresponding α-metalated alkylbenzenes. Treatment of the latter in succession with solid carbon dioxide, water, and hydrochloric acid gave carboxylic or dicarboxylic acids in 65–78% yield. Metalation of isopropylbenzene with sodium or potassium crown ether complexes above 90°C was accompanied by cleavage of the polyether ring with formation of organometallic compounds which then reacted with isopropylbenzene to produce 2-sodio(potassio)-2-phenylpropane and open-chain oligoether.


Crown Ether Cumene Concentrate Hydrochloric Acid Aqueous Alkali Crown Ether Complex 
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Copyright information

© Pleiades Publishing, Ltd. 2009

Authors and Affiliations

  • A. L. Shabanov
    • 1
  • N. M. Seidov
    • 1
  • U. A. Gasanova
    • 2
  • Z. O. Kakhramanova
    • 1
  • M. M. Gasanova
    • 1
  1. 1.Research Institute of Petroleum and Gas Geotechnology Problems and ChemistryAzerbaidjan State Petroleum AcademyBakuAzerbaidjan
  2. 2.Azerbaidjan Medical UniversityBakuAzerbaidjan

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