Dioxime oxalates; new iminyl radical precursors for syntheses of N-heterocycles

Fernando Portela Cubillo, James Lymer, Eoin Martin Scanlan, J. S. Scott, John Christopher Walton*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

46 Citations (Scopus)

Abstract

Symmetrical and unsymmetrical dioxime oxalates were prepared by treatment of oximes with oxalyl chloride. UV photolysis of these precursors was found to be an atom-efficient way of generating iminyl radicals. The process was most efficient for dioxime oxalates having aryl substituents attached to their Cdouble bond; length as m-dashN bonds. The method was useful for EPR spectroscopic study of iminyl and iminoxyl radicals. Photolyses in toluene solution, of dioxime oxalates containing alkenyl acceptor groups, yielded unsaturated iminyl radicals that ring closed to afford 3,4-dihydro-2H-pyrroles in good yields. Dioxime oxalates with biphenyl substituents also released iminyl radicals that ring closed onto the aromatic acceptor groups and, in acetonitrile solution, this approach provided a useful and atom-efficient method of making substituted phenanthridines.
Original languageEnglish
Pages (from-to)11908-11916
Number of pages9
JournalTetrahedron
Volume64
Issue number52
Early online date20 Sept 2008
DOIs
Publication statusPublished - 22 Dec 2008

Keywords

  • Dihydropyrroles
  • Oximes
  • Phenanthridines
  • Radical cyclization

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