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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 cis - N -Ts iodoaziridines by activation of the C-I bond using alkoxides as a source of single electrons. These form predominantly trans -substituted selenoaziridines dependent on the size of the diselenide. cis -Aziridinyllithiums generated by Li-I exchange also react with diselenides stereospecifically to form a range of cis -selenoaziridines. Proposals for the stereochemical outcome are presented.

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