Nitrones and oxaziridines. XXX. Double ring cleavage of bicyclic oxaziridines by iron(II) sulfate

Abstract

The hydroxy oxaziridines (7), (10), (13), (16) and (23) have been converted by iron(11) sulfate into the respective amides (8), (11), (14), (17) and (24). The oxaziridines were generated from the corresponding I-pyrroline 1-oxides (6), (9), (12), (15) and (22) and in some cases were not characterized but converted directly into the amides. Two isomers of oxaziridine (7) were isolated, only one of which was formed in the peracetic acid oxidation of the pyrroline (5). The oxaziridine (23) was isolated and characterized as a mixture of two isomers.