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The Reaction between Diphenylmethane and Butadiene with Organolithium Compounds

Abstract

The reaction between diphenylmethane and butadiene with organolithium compounds was investigated in order to obtain telomers containing one butadiene unit in high selectivity. The lithium salt of methoxyethanol (CH3OCH2CH2OLi), N,N,N′,N′-tetramethylethylenediamine(TMEDA), hexamethylphosphoric triamide(HMPT) and their related compounds were used as complexing agents for lithium alkyl. 5,5-Diphenyl-2-pentene and 5,5-diphenyl-1-pentene (DPPE) were obtained in high yields using these catalyst systems. The influence of molar ratio, [complexing agent]/[lithium alkyl], on the yield of DPPE was studied and the reaction was found to depend strongly on the nature of complexing agent. In order to discuss the specificity of the various catalyst systems, the metalation reaction of diphenylmethane was investigated.

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Yamaguchi, T., Narita, T. & Tsuruta, T. The Reaction between Diphenylmethane and Butadiene with Organolithium Compounds. Polym J 3, 573–580 (1972). https://doi.org/10.1295/polymj.3.573

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Keywords

  • Anionic Telomerization
  • Butadiene
  • Diphenylmethane
  • n-Butyllithium
  • Methoxyethanol
  • N,N,N′,N′-Tetramethylethylenediamine
  • Hexamethylphosphoric Triamide
  • 5,5-Diphenyl-2-pentene

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