Synthesis of 4'-alkyl-[1,1'-biphenyl]-2,3'-dicarbonitriles via dimerisation of phthalonitrile radical anion in liquid ammonia

Roman Yu Peshkov, Chunyan Wang, Elena V. Panteleeva, Evgeny V. Tretyakov

Research output: Contribution to journalArticlepeer-review

Abstract

Single-electron reduction of phthalonitrile by metallic lithium in liquid ammonia resulted in a radical anion salt that underwent dimerisation yielding a long-lived intermediate, the 1,2-dicyano-4-(2-cyanophenyl)cyclohexa-2,5-dienyl anion. Alkylation of this anion with primary alkyl iodides resulted in a convenient one-pot synthesis of 4'-alkyl-[1,1'-biphenyl]-2,3'-dicarbonitriles.

Original languageEnglish
Pages (from-to)349-356
Number of pages8
JournalArkivoc
Volume2018
Issue number7
DOIs
Publication statusPublished - 25 Nov 2018

Keywords

  • Biphenyl-2,3'-dicarbonitriles
  • Dimerisation
  • Phthalonitrile
  • Radical anions
  • Reductive alkylation
  • MOLDEN
  • dimerisation
  • TEREPHTHALONITRILE DIANION
  • radical anions
  • ARENES
  • FRAMEWORKS
  • biphenyl-2,3 '-dicarbonitriles
  • REDUCTIVE ACTIVATION
  • reductive alkylation

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