1101835-41-9Relevant academic research and scientific papers
Dioxime oxalates; new iminyl radical precursors for syntheses of N-heterocycles
Portela-Cubillo, Fernando,Lymer, James,Scanlan, Eoin M.,Scott, Jackie S.,Walton, John C.
experimental part, p. 11908 - 11916 (2009/04/06)
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 C{double bond, long}N 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.
From dioxime oxalates to dihydropyrroles and phenanthridines via iminyl radicals
Portela-Cubillo, Fernando,Scanlan, Eoin M.,Scott, Jackie S.,Walton, John C.
scheme or table, p. 4189 - 4191 (2009/03/11)
Dioxime oxalates are useful precursors for the clean generation of iminyl radicals by sensitised UV photolysis and can be adapted for serviceable preparations of 3,4-dihydro-2H-pyrroles and phenanthridines. The Royal Society of Chemistry.
