Synthesis of Selenoaziridines: A Study on Stereochemical Outcomes of the Reaction of Aziridine Radicals and Anions Generated from Iodoaziridines.

The synthesis of a new functional group in the form of selenyl-substituted aziridines is described. Selenoaziridines are stereoselectively prepared by functionalization of intact aziridine precursors involving radical and anionic intermediates. Radicals are generated from --Ts iodoaziridines by activation of the C-I bond using alkoxides as a source of single electrons. These form predominantly -substituted selenoaziridines dependent on the size of the diselenide. -Aziridinyllithiums generated by Li-I exchange also react with diselenides stereospecifically to form a range of -selenoaziridines. Proposals for the stereochemical outcome are presented.