Russian Journal of Organic Chemistry

, Volume 49, Issue 4, pp 530–535 | Cite as

Methyl (E)-2-(2-phenylcyclopropylidene)acetate: Synthesis, isomerization, and reaction with 1,3-diphenyl-2-benzofuran

  • A. P. Molchanov
  • T. Q. Tran
  • A. V. Stepakov
  • V. V. Gurzhii
  • R. R. Kostikov
Article

Abstract

Treatment of 3-methyl-2-phenylcycloprop-2-ene-1-carboxylic acid with potassium tert-butoxide induced its isomerization into trans-2-methylidene-3-phenylcyclopropane-1-carboxylic acid which was converted into methyl ester, and heating of the latter for 1 h in toluene gave methyl (E)-2-(2-phenylcyclopropylidene)acetate. Thermal isomerization of methyl (E)-2-(2-phenylcyclopropylidene)acetate on prolonged heating in toluene afforded 5-methoxy-3-methyl-2-phenylfuran, and the reaction with 1,3-diphenyl-2-benzofuran resulted in [4 + 2]-cycloaddition at the exocyclic double bond.

Keywords

Thermal Isomerization Diazoacetate Acid Versus Exocyclic Double Bond Phenylallene 

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Copyright information

© Pleiades Publishing, Ltd. 2013

Authors and Affiliations

  • A. P. Molchanov
    • 1
  • T. Q. Tran
    • 2
  • A. V. Stepakov
    • 1
  • V. V. Gurzhii
    • 1
  • R. R. Kostikov
    • 1
  1. 1.St. Petersburg State UniversitySt. PetersburgRussia
  2. 2.Hanoi University of Science and TechnologyHa NoiViet Nam

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