Synthesis of isoindoline nitroxides by electrocyclic reactions

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Abstract

The Suzuki reaction of the pyrroline nitroxide, 3-bromo-4-formyl-2,2,5,5- tetramethyl-2,5-dihydro-1H-pyrrol-1-yloxyl radical, with vinylboronic acids and subsequent Horner-Wadsworth-Emmons reaction followed by electocyclic reaction of the thus formed 1,3,5-triene and oxidation offers a new route for the synthesis of 5,6-disubstituted 1,1,3,3-tetramethylisoindolin-2-yloxyl radicals. The alternative Diels-Alder reaction pathway sometimes resulted in poor yields. Starting from 5-(ethoxycarbonyl)-1,1,3,3-tetramethyl-6-phenylisoindolin-2-yloxyl radical we obtained a spin-labeled fluorenone.

Original languageEnglish
Article numberP05009SS
Pages (from-to)2591-2595
Number of pages5
JournalSynthesis
Issue number15
DOIs
Publication statusPublished - Aug 1 2009

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Keywords

  • Cross-coupling
  • Diels-Alder reaction
  • Electrocyclic reaction
  • Free radical
  • Wittig reaction

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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