Electron transfer induced dissociations of 2- and 4-alkyl cyclohexadienones

Andrew McCarroll, Joseph Alan Crayston, John Christopher Walton

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

Several 2- and 4-alkylcyclohexadienones were prepared and shown to accept electrons to produce ketyl radical anions that dissociated rapidly at room temperature to release carbon-centered radicals and an aromatic phenoxide type anion. In the PET process with benzyl-substituted cyclohexadienones, initiated with triethylamine, the benzyl radicals dimerised or abstracted an H-atom from solvent. In electrochemical reductions, and in reductions with alkali metals in liquid ammonia, the benzyl radicals were further reduced to anions. (C) 2003 Elsevier Science Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)4275-4280
Number of pages6
JournalTetrahedron
Volume59
Issue number24
DOIs
Publication statusPublished - 9 Jun 2003

Keywords

  • free radicals
  • electron transfer
  • cyclohexadienones
  • Birch reductions
  • RADICAL-ION PROBES
  • SILYLATED CYCLOHEXADIENES
  • AMINOACYL RADICALS
  • CYCLOHEXA-1,4-DIENE-3-CARBOXYLATES
  • 2,5-DIHYDROFURAN-2-CARBOXYLATES
  • CYCLIZATION
  • GENERATION
  • CHEMISTRY

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