Reactions of (E)-2-tert-Butyl-3-phenyloxaziridine with Lithium Amide

Article abstract of DOI:10.1021/jo01296a029

The reactions of (E)-2-tert-butyl-3-phenyloxaziridine (1a) with lithium amide bases in tetrahydrofuran have been studied.In competing rections, 1a is reduced to N-tert-butylbenzaldimine (2) and isomerized to N-tert-butylbenzamide (3).The former reaction proceeds through an intermediate which accumulates and slowly decomposes to 2; the reaction apparently occurs via an initial electron transfer from the base to the oxaziridine.The latter reaction occurs by simultaneous deprotonation and ring opening of the oxaziridine to give the anion of 3.