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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
Article

Abstract

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.

Keywords

Crown Ether Cumene Concentrate Hydrochloric Acid Aqueous Alkali Crown Ether Complex 
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

© 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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